Water → 5-(acetylamino)-2-chlorobenzoic acid

HRID 1662851Notes

Reaction equation

HRID 1662851 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].[C:12](Cl)(=[O:14])[CH3:13].C(N(CC)CC)C.O>C(Cl)Cl>[C:12]([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:14])[CH3:13]

Participants

6

Reactant 4

HCID 962WaterHCID 6367Acetyl chlorideHCID 8471TriethylamineHCID 378795-Amino-2-chlorobenzoic acid

Product 1

HCID 6809565-(acetylamino)-2-chlorobenzoic acidYield 27.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 5-amino-2-chloro-benzoic acid (0.50 g, 2.9 mmol) in DCM (15 mL) was added acetyl chloride (0.30 mL, 4.2 mmol) followed by triethylamine (1.2 mL, 8.6 mmol). The mixture was stirred at RT for 2 h and poured into water. The mixture was extracted with ethyl acetate and the combined organic layers washed with water, brine, dried over Na2SO4 and filtered. The filtrate was concentrated and afforded the title compound (0.17 g, 27%) as a brown solid.

Workup

  1. extractionThe mixture was extracted with ethyl acetate
  2. washthe combined organic layers washed with water, brine
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationThe filtrate was concentrated

Sources & evidence

ORD record
ord-90978966fcd446c98fa9f061fd3034c8
Source dataset
uspto-grants-2011_10
Patent number
US08030487B2

Reaction notes

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