Methylamine → 4-(Methylamino)-3-nitrobenzoic acid

HRID 1527141Notes

Reaction equation

HRID 1527141 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].[CH3:14][NH2:15]>>[CH3:14][NH:15][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]

Participants

3

Reactant 2

HCID 6329MethylamineHCID 73204-Chloro-3-nitrobenzoic acid

Product 1

HCID 2834754-(Methylamino)-3-nitrobenzoic acid

Procedure

300 g (1.49 mol) of 4-chloro-3-nitrobenzoic acid were suspended in 769 g of a 25-30% aqueous solution of methylamine. After heating to reflux temperature, a clear solution was obtained. The solution was kept at reflux temperature for 2 hours and total consumption of 4-chloro-3-nitrobenzoic acid was checked by TLC. The solution was cooled to room temperature, and pH was adjusted to about 1 by addition of 2M aqueous sulphuric acid. Precipitation of a yellow solid was observed, which was isolated by filtration. The filtered cake was washed with water and subsequently with methanol to obtain 331 g of wet 4-(methylamino)-3-nitrobenzoic acid as a yellow powder. Purity (HPLC, method 2): 99.1%.

Workup

  1. temperatureAfter heating
  2. temperatureto reflux temperature
  3. customa clear solution was obtained
  4. temperatureat reflux temperature for 2 hours
  5. customtotal consumption of 4-chloro-3-nitrobenzoic acid
  6. additionpH was adjusted to about 1 by addition of 2M aqueous sulphuric acid
  7. customPrecipitation of a yellow solid
  8. customwhich was isolated by filtration
  9. washThe filtered cake was washed with water and subsequently with methanol

Sources & evidence

ORD record
ord-df0d191e3042453b8ccb70bff9fb2b94
Source dataset
uspto-grants-2015_07
Patent number
US09086390B2

Reaction notes

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