Methanol → 2-[(3-Chloro-4-methoxybenzoyl)amino]benzoic acid

HRID 2099970Notes

Reaction equation

HRID 2099970 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:18]=[CH:19][C:20]=1[O:21][CH3:22])[C:5]([NH:7][C:8]1[CH:17]=[CH:16][CH:15]=[CH:14][C:9]=1[C:10]([O:12]C)=[O:11])=[O:6].CO>C1COCC1.O>[Cl:1][C:2]1[CH:3]=[C:4]([CH:18]=[CH:19][C:20]=1[O:21][CH3:22])[C:5]([NH:7][C:8]1[CH:17]=[CH:16][CH:15]=[CH:14][C:9]=1[C:10]([OH:12])=[O:11])=[O:6]

Participants

5

Reactant 2

HCID 887MethanolHCID 800035Methyl 2-(3-chloro-4-methoxybenzamido)benzoate

Product 1

HCID 8914522-[(3-Chloro-4-methoxybenzoyl)amino]benzoic acidYield 85%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of 42A (340 mg, 1.1 mmol) in THF (30 mL)/MeOH (10 mL) was treated with a solution of LiOH monohydrate (223 mg, 5.3 mmol) in water (10 mL). The reaction was stirred for 24 hours at room temperature and concentrated to a yellow solid. The crude acid was dissolved in water (100 mL) and acidified with 1 N HCl to pH 4. The resulting solid was collected by vacuum filtration and washed with water (2×100 mL) to afford 42B (260 mg, 85%).

Workup

  1. concentrationconcentrated to a yellow solid
  2. dissolutionThe crude acid was dissolved in water (100 mL)
  3. filtrationThe resulting solid was collected by vacuum filtration
  4. washwashed with water (2×100 mL)

Sources & evidence

ORD record
ord-9fc9c0e848184a03a5202cc664e60239
Source dataset
uspto-grants-2009_08
Patent number
US07569725B2

Reaction notes

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