4-Chloro-3-nitrobenzoic acid → 4-(Butylamino)-3-nitrobenzoic acid

HRID 2166033Notes

Reaction equation

HRID 2166033 reaction equation
Cl[C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[CH:4][C:3]=1[N+:11]([O-:13])=[O:12].[CH2:14]([NH2:18])[CH2:15][CH2:16][CH3:17]>>[CH2:14]([NH:18][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[CH:4][C:3]=1[N+:11]([O-:13])=[O:12])[CH2:15][CH2:16][CH3:17]

Participants

3

Reactant 2

HCID 73204-Chloro-3-nitrobenzoic acidHCID 8007Butylamine

Product 1

HCID 28298164-(Butylamino)-3-nitrobenzoic acidYield 100%

Procedure

A mixture of 50 parts of 4-chloro-3-nitrobenzoic acid and 222 parts of 1-butanamine was stirred for 3 hours at reflux temperature. After cooling and evaporation of the excess of 1-butanamine, the reaction mixture was acidified with a sulfuric acid solution 2N to pH 1. The precipitated product was filtered off and dried, yielding 59 parts (100%) of 4-(butylamino)-3-nitrobenzoic acid (int. 7).

Workup

  1. temperatureat reflux temperature
  2. temperatureAfter cooling
  3. customevaporation of the excess of 1-butanamine
  4. filtrationThe precipitated product was filtered off
  5. customdried

Sources & evidence

ORD record
ord-9ff8b545f17f4243a450a5754f6fb66b
Source dataset
uspto-grants-1990_07
Patent number
US04943574

Reaction notes

Loading…