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

HRID 252858Notes

Reaction equation

HRID 252858 reaction equation
[CH3:1][NH2:2].O.F[C:5]1[CH:13]=[CH:12][C:8]([C:9]([OH:11])=[O:10])=[CH:7][C:6]=1[N+:14]([O-:16])=[O:15]>CN(C=O)C>[CH3:1][NH:2][C:5]1[CH:13]=[CH:12][C:8]([C:9]([OH:11])=[O:10])=[CH:7][C:6]=1[N+:14]([O-:16])=[O:15]

Participants

5

Reactant 3

HCID 962WaterHCID 6329MethylamineHCID 679874-Fluoro-3-nitrobenzoic acid

Product 1

HCID 2834754-(Methylamino)-3-nitrobenzoic acidYield 100%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A 40% solution of methylamine in water (11 mL; 128 mmol) (or any other primary amine) was slowly added to a stirring suspension of 4-fluoro-3-nitrobenzoic acid (278, 6.1 g; 32.9 mmol) in DMF (20 mL) at room temperature. After the addition was completed the mixture was stirred at the same temperature for 60 min; concentrated in vacuo, and suspended in 5% KHSO4 (final pH=2). The suspension was stirred overnight; the precipitate was collected by filtration, washed with water, then with ether and dried to afford the title compound 279 (6.5 g; 100% yield). 1H NMR: (400.2 MHz, DMSO) δ (ppm): 12.8 (bs; 1H), 8.59 (d, J=2.0 Hz; 1H); 8.55 (q, J=5.0 Hz; 1H); 7.96 (dd, J=2.0, 9.1 Hz; 1H); 7.04 (d, J=9.1 Hz; 1H); 3.00 (d, J=5.0 Hz; 3H). MS: calc: 196.2; found: 197.1 (M+H)

Workup

  1. additionAfter the addition
  2. concentrationconcentrated in vacuo
  3. stirringThe suspension was stirred overnight
  4. filtrationthe precipitate was collected by filtration
  5. washwashed with water
  6. dry with materialwith ether and dried

Sources & evidence

ORD record
ord-530bcd613205464fa33ccf126ac3574c
Source dataset
uspto-grants-2011_01
Patent number
US07868205B2

Reaction notes

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