Acetyl chloride → 1422206-15-2

HRID 1505775Notes

Reaction equation

HRID 1505775 reaction equation
[Br:1][C:2]1[CH:10]=[C:6]([C:7]([OH:9])=[O:8])[C:5]([NH2:11])=[C:4]([OH:12])[CH:3]=1.[C:13](Cl)(=O)[CH3:14].C(N(CC)CC)C.C1(C)C=CC(S([O-])(=O)=O)=CC=1.[NH+]1C=CC=CC=1>C1(C)C(C)=CC=CC=1.C(OCC)(=O)C>[Br:1][C:2]1[CH:3]=[C:4]2[O:12][C:13]([CH3:14])=[N:11][C:5]2=[C:6]([C:7]([OH:9])=[O:8])[CH:10]=1

Participants

7

Reactant 4

HCID 6367Acetyl chlorideHCID 8471TriethylamineHCID 466102Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1)HCID 217551432-Amino-5-bromo-3-hydroxybenzoic Acid

Product 1

HCID 840315161422206-15-2

Reagents, catalysts & solvents 2

HCID 7237O-XyleneSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 5-bromo-3-hydroxyanthranilic acid (prepared as described in Eur. J. Med. Chem., 1999, 34, 729) (400 mg) in xylene (30 mL), were added acetyl chloride (135 μL), triethylamine (265 μL) and pyridinium p-toluenesulfonate (130 mg), and the mixture was heated at reflux for 8 hours. The reaction mixture was cooled to room temperature, diluted with ethyl acetate, washed sequentially with water and brine, and dried over anhydrous magnesium sulfate, and the solvent was removed under reduced pressure. The residue was purified on silica gel column chromatography to obtain the titled compound (471 mg).

Workup

  1. temperaturethe mixture was heated
  2. temperatureat reflux for 8 hours
  3. washwashed sequentially with water and brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customthe solvent was removed under reduced pressure
  6. customThe residue was purified on silica gel column chromatography

Sources & evidence

ORD record
ord-4ab6c08a45ca4593b95424bfdadcbbc9
Source dataset
uspto-grants-2015_12
Patent number
US09216968B2

Reaction notes

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