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C4H5N See also:PYRROL or C41;T4•NH, an organic See also:base found in See also:coal-See also:tar and See also:Dippel's oil . It may be synthetically prepared by the dry See also:distillation of ammonium mucate, or, better, by See also:heating it with See also:glycerin to 180-200° C . (H . Schwanert, See also:Ann., 186o, 116, p . 257); by passing the vapour of diethylamine through a red-hot See also:tube; by distilling succinimide with See also:zinc dust (C . A . See also:Bell, Ber., 188o, 13, p . 877); by distilling See also:calcium pyroglutaminate: H02C' CH(See also:NH2)'See also:CH2'CH2 See also:CO2H = C4H4NH+See also:CO2+2H20 (L . Haitinger, Monats., 1882, 3, p . 228); and by boiling succinic dialdehyde.with See also:ammonia and glacial acetic See also:acid (C . Harries, Ber., 1901, 34, p . 1497) .
It is a feebly basic, colourless liquid which boils at 13o° C., and possesses a See also:smell resembling that of See also:chloroform
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It is slightly soluble in See also:water, and turns See also: Hydriodic acid at high temperature reduces pyrrol to pyrrolidine (tetra-hydropyrrol), C4HSNH . Pyrrolidine has also been prepared by A . Thiele (Ber., 1905, 38, p . 4Ip4) from ,B-chlorpropionic aldehyde diethyl acetal . The See also:chlorine See also:atom in this See also:compound is replaced by the cyano-group, which is then reduced to. the CH2NH2. group and coupled up with See also:benzene sulphochloride to See also:form the compound C6H5S02NH(CH2)2.CH(OC2H6)2• This substance easily splits out See also:alcohol, and the ring compound then formed yields pyrrolidine on reduction by See also:sodium in amyl alcohol solution . An a-pyrrolidine carboxylic acid and its hydroxy derivatives have been detected by E . See also:Fischer among the products of See also:hydrolysis of proteids . R . Willstatter (Ber., 1900, 33, p . 1164) obtained this acid by the action of a methyl alcoholic solution of ammonia on dibrompropylmalonic ester at 140° C., the diamide formed being then hydrolysed either by hydrochloric acid or baryta water : CH2•CBr(CO2H)2 CH2• (CONH2) CH2• CH(CO2H) I —s I )NH—a >NH . CH2•CH2Br CH2 CH2 CH2 CH2 Numerous substitution derivatives of pyrrol are known . The N-derivatives are prepared by the action of alkyl halides and acid chlorides on potassium pyrrol . The C-derivatives have been prepared in various ways . L . Knorr, by the action of ammonia on aceto-acetic ester, obtained 19-imidobutyric ester, which with nitrous acid yields a-isonitroso-$-imidobutyric ester, See also:CH3.C(:NH)•C(:N•OH)•CO2C2H6 . Reduction of this ester leads to the formation of ammonia, hydroxylamine, and dimethyl pyrrol dicarboxylic ester, HN/C(CH3) : C44 •CO2R \C(CO2R) :C•CH3• He also found that diaceto succinic ester reacts with compounds of the type NH2R(R=H, CH2, OH, NHC6H6, &c.) to form pyrrol derivatives :propionic acid with 'hydroxylamine . It is monobasic and yields salts which only crystallize with See also:great difficulty; when liberated from these salts by a mineral acid it forms a syrupy non-volatile See also:mass . In aqueous solution it gives a red See also:colour with ferric chloride . It shows characteristic ketone reactions, yielding a bisulphite compound and combining with hydro-cyanic acid to form the nitrile of a-oxyisosuccinic acid . When warmed with baryta water it gives uvitic acid . Pyruvic nitrile, or acetyl See also:cyanide, See also:CH3CO•CN, may be prepared by the action of See also:silver cyanide on acetyl chloride ; or of acetyl chloride on nitrosoacetone (L . Claisen and O . Manasse, Ber., .1887, 2o, p . 2196) . It is a liquid which boils at 93° C. and with See also:caustic alkalis polymerizes to diacetyldicyanide . |
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[back] PYRRHUS (c. 318–272 B.C.) |
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