Hydrochloric Acid → 2'-Chloro-4'-nitrovaleranilide

HRID 46494

Reaction equation

HRID 46494 reaction equation
[C:1](Cl)(=[O:6])[CH2:2][CH2:3][CH2:4][CH3:5].[Cl:8][C:9]1[CH:15]=[C:14]([N+:16]([O-:18])=[O:17])[CH:13]=[CH:12][C:10]=1[NH2:11].Cl>N1C=CC=CC=1>[Cl:8][C:9]1[CH:15]=[C:14]([N+:16]([O-:18])=[O:17])[CH:13]=[CH:12][C:10]=1[NH:11][C:1](=[O:6])[CH2:2][CH2:3][CH2:4][CH3:5]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 84922-Chloro-4-nitroanilineHCID 61186Valeryl chloride

Product 1

HCID 36282822'-Chloro-4'-nitrovaleranilide

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

Valeryl chloride (12.06 g., 0.10 mole) is added dropwise to a cooled stirred solution of 2-chloro-4-nitroaniline (17.26 g., 0.10 mole) in pyridine (100 ml.). The mixture is warmed to ambient temperature, then heated (80°-100° C.) for twenty-four hours. The cooled solution is poured into cold 1 N hydrochloric acid (500 ml.) with stirring. The precipitated solid is collected, washed well with water and dried, 25.1 g., m.p. 80°-95° C. Recrystallization from cyclohexane yeilds material (19.75 g.) of m.p. 95°-97° C.

Workup

  1. temperatureheated (80°-100° C.) for twenty-four hours
  2. customThe precipitated solid is collected
  3. washwashed well with water
  4. customdried
  5. customRecrystallization from cyclohexane yeilds material (19.75 g.) of m.p. 95°-97° C.

Sources & evidence

ORD record
ord-4d1f016b8e124e3ba94a22611145c877
Source dataset
uspto-grants-1979_11
Patent number
US04173646

Linked notes

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