Acetyl chloride → Methyl 3-Amino-4-chlorobenzoate

HRID 272561Notes

Reaction equation

HRID 272561 reaction equation
[Cl:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[CH:4][C:3]=1[NH2:11].[C:12](Cl)(=O)C>CO>[Cl:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([O:8][CH3:12])=[O:7])=[CH:4][C:3]=1[NH2:11]

Participants

4

Reactant 2

HCID 6367Acetyl chlorideHCID 760923-Amino-4-chlorobenzoic acid

Product 1

HCID 593055Methyl 3-Amino-4-chlorobenzoate

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
70 °C

Procedure

To a solution of 4-chloro-3-amino-benzoic acid (10.0 g, 58.3 mmol) in methanol (50 mL) was added acetyl chloride (13.0 mL) dropwise at room temperature. After the addition, the reaction mixture was heated at 70° C. for 3 h and then cooled to room temperature. The solvent was removed under reduced pressure and water (100 mL) was added. The resulting solution was neutralized with NaHCO3 followed by extraction with EtOAc (3×100 mL). The combined organic layers were dried (MgSO4) and concentrated in vacuum to afford a yellow oil (22, 10.5 g, 97%). 1H NMR (DMSO-d6, 300 MHz) δ 7.41 (??d, J=2.1 Hz, 1H), 7.31 (d, J=8.4 Hz, 1H), 7.09 (dd, J=2.1, 8.4 Hz, 1H), 5.66 (br s, 2H), 3.80 (s, 3H).

Workup

  1. additionAfter the addition
  2. temperaturecooled to room temperature
  3. customThe solvent was removed under reduced pressure and water (100 mL)
  4. additionwas added
  5. extractionfollowed by extraction with EtOAc (3×100 mL)
  6. dry with materialThe combined organic layers were dried (MgSO4)
  7. concentrationconcentrated in vacuum
  8. customto afford a yellow oil (22, 10.5 g, 97%)

Sources & evidence

ORD record
ord-0cee1c864a20495cba821184f621b338
Source dataset
uspto-grants-2008_11
Patent number
US07456178B2

Reaction notes

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