Hydrochloric Acid → 3-(Methylamino)-4-nitrobenzoic acid

HRID 412702Notes

Reaction equation

HRID 412702 reaction equation
[N+:1]([C:4]1[CH:12]=[CH:11][C:7]([C:8]([OH:10])=[O:9])=[CH:6][C:5]=1OC)([O-:3])=[O:2].[CH3:15][NH2:16].Cl>>[CH3:15][NH:16][C:5]1[CH:6]=[C:7]([CH:11]=[CH:12][C:4]=1[N+:1]([O-:3])=[O:2])[C:8]([OH:10])=[O:9]

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 6329MethylamineHCID 787643-Methoxy-4-nitrobenzoic acid

Product 1

HCID 221846233-(Methylamino)-4-nitrobenzoic acidYield 73%

Conditions

Temperature
100 °C

Procedure

A mixture comprising 4-nitro-3-methoxybenzoic acid (5.0 g, 25.4 mmol) and aqueous methylamine (40%, 15 mL) is a sealed tube was heated in an oil bath at 100° C. for 12 hours, allowed to cool to room temperature, and then poured into a stirring slurry of 1M aqueous hydrochloric acid and ice to give an orange precipitate. The precipitate was collected by filtration, rinsed with water and recrystallized from hot ethanol to provide 3-methylamino-4-nitrobenzoic acid as a bright red crystalline solid (3.6 g, 73% yield); 1H-NMR (300 MHz, DMSO-d6): 13.5 (s), 8.3 (q), 8.2 (d), 7.4 (s), 7.1 (d), 3.0 (d).

Workup

  1. temperatureto cool to room temperature
  2. customto give an orange precipitate
  3. filtrationThe precipitate was collected by filtration
  4. washrinsed with water
  5. customrecrystallized from hot ethanol

Sources & evidence

ORD record
ord-d353319eaea84c35ba97bca3607701d0
Source dataset
uspto-grants-2003_05
Patent number
US06562854B2

Reaction notes

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