5-Amino-2-chlorobenzoic acid → 5-(3-Methylbenzamido)-2-Chlorobenzoic Acid

HRID 1662804Notes

Reaction equation

HRID 1662804 reaction equation
[NH2:1][C:2]1[CH:3]=[CH:4][C:5]([Cl:11])=[C:6]([CH:10]=1)[C:7]([OH:9])=[O:8].[CH3:12][C:13]1[CH:14]=[C:15]([CH:19]=[CH:20][CH:21]=1)[C:16](Cl)=[O:17]>C1COCC1>[CH3:12][C:13]1[CH:14]=[C:15]([CH:19]=[CH:20][CH:21]=1)[C:16]([NH:1][C:2]1[CH:3]=[CH:4][C:5]([Cl:11])=[C:6]([CH:10]=1)[C:7]([OH:9])=[O:8])=[O:17]

Participants

4

Reactant 2

HCID 378795-Amino-2-chlorobenzoic acidHCID 743753-Methylbenzoyl chloride

Product 1

HCID 286666905-(3-Methylbenzamido)-2-Chlorobenzoic AcidYield 81.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirring solution of 5-amino-2-chlorobenzoic acid (880 mg, 5.1 mmol) in anhydrous THF (45 mL), 3-methylbenzoyl chloride (870 mg, 5.6 mmol) was added slowly. The mixture was stirred at room temperature under argon for overnight. The solvent was removed under reduced pressure and re-crystallized from chloroform to afford the title compound as a white solid (1.2 g, 80%).

Workup

  1. customThe solvent was removed under reduced pressure
  2. customre-crystallized from chloroform

Sources & evidence

ORD record
ord-c232b297f9f6445085c269bd8a0a2278
Source dataset
uspto-grants-2011_10
Patent number
US08030487B2

Reaction notes

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