2-Methyl-5-Nitroaniline → HCID 18505064, compound

HRID 1357022Notes

Reaction equation

HRID 1357022 reaction equation
[K].Br[C:3]1[CH:11]=[CH:10][C:9]([O:12][CH3:13])=[CH:8][C:4]=1[C:5]([OH:7])=[O:6].[CH3:14][C:15]1[CH:21]=[CH:20][C:19]([N+:22]([O-:24])=[O:23])=[CH:18][C:16]=1[NH2:17].[OH-].[K+]>O.[Cu]>[CH3:14][C:15]1[CH:21]=[CH:20][C:19]([N+:22]([O-:24])=[O:23])=[CH:18][C:16]=1[NH:17][C:3]1[C:4](=[CH:8][C:9]([O:12][CH3:13])=[CH:10][CH:11]=1)[C:5]([OH:7])=[O:6]

Participants

7

Reactant 4

HCID 74442-Methyl-5-NitroanilineHCID 14797Potassium HydroxideHCID 899062-Bromo-5-methoxybenzoic acidHCID 5462222Potassium

Product 1

HCID 18505064HCID 18505064, compoundYield 56%

Reagents, catalysts & solvents 2

HCID 23978CopperCatalystHCID 962WaterSolvent

Procedure

Potassium salt of 2-bromo-5-methoxybenzoic acid (23 g) and 2-methyl-5-nitroaniline (40 g) are stirred and heated at 110° C. in the presence of 50 mg of catalytic copper for 50 minutes. Next, the reaction mixture is poured on 5% solution of potassium hydroxide in water (600 ml) and cooled. The formed precipitate is filtered off, washed with water, and the collected solutions are acidified with hydrochloric acid to pH 5. The formed solid is filtered off and crystallized from methanol-acetone (2:1) to give N-(2′-methyl-5′-nitrophenyl)-5-methoxyanthranilic acid (11.2 g, 56% yield), m.p. 219-221° C. 1H NMR (d6 DMSO): δ9.20 (bs, 1H), 7.88 (d, 1 H, J=1.9 Hz), 7.65 (dd, 1 H, J1=7.8 Hz, J2=1.9 Hz), 7.44 (d, 1 H, J=8.3 Hz), 7.43 (d, 1 H, J=2.9 Hz), 7.26 (d, 1 H, J=8.8 Hz), 7.19 (dd, 1H, J1=8.8 Hz, J2=2.9 Hz), 3.68 (s, 3 H), 2.27 (s, 3 H).

Workup

  1. temperaturecooled
  2. filtrationThe formed precipitate is filtered off
  3. washwashed with water
  4. filtrationThe formed solid is filtered off
  5. customcrystallized from methanol-acetone (2:1)

Sources & evidence

ORD record
ord-e0d2ee8db44e48bb98fba51538643c89
Source dataset
uspto-grants-2003_07
Patent number
US06589961B2

Reaction notes

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