Hydrochloric Acid → HCID 12912435, compound

HRID 1680832Notes

Reaction equation

HRID 1680832 reaction equation
[NH2:1][C:2]1[C:10]([CH3:11])=[C:9]([C:12]([O:14][CH2:15][CH3:16])=[O:13])[C:8]([CH3:17])=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].N1C=CC=CC=1.[C:24](Cl)(=[O:26])[CH3:25].Cl>C1C=CC=CC=1>[C:24]([NH:1][C:2]1[C:10]([CH3:11])=[C:9]([C:12]([O:14][CH2:15][CH3:16])=[O:13])[C:8]([CH3:17])=[CH:7][C:3]=1[C:4]([OH:6])=[O:5])(=[O:26])[CH3:25]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 1049PyridineHCID 6367Acetyl chlorideHCID 12685839HCID 12685839, compound

Product 1

HCID 12912435HCID 12912435, compoundYield 71.4%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent2×

Procedure

To a mixture consisting of 1 g of 2-amino-4-ethoxycarbonyl-3,5-dimethylbenzoic acid, 20 ml of dry benzene, and 0.7 ml of pyridine in a flask cooled with ice water was added dropwise with stirring a solution of 450 mg of acetyl chloride in 5 ml of benzene. The reaction mixture was stirred overnight, and then shaken with dilute hydrochloric acid. The layers were separated. The acidic aqueous layer was extracted with ethyl acetate, and the combined organic extracts were washed with water, and dried over sodium sulfate. The solvent was removed by distillation. The residue was recrystallized from ethyl acetate to afford 0.84 g of 2-acetylamino-4-ethoxycarbonyl-3,5-dimethylbenzoic acid melting at 164° C.

Workup

  1. additionwas added dropwise
  2. customThe layers were separated
  3. extractionThe acidic aqueous layer was extracted with ethyl acetate
  4. washthe combined organic extracts were washed with water
  5. dry with materialdried over sodium sulfate
  6. customThe solvent was removed by distillation
  7. customThe residue was recrystallized from ethyl acetate

Sources & evidence

ORD record
ord-947a78a9884e4166bd1b37a8b98fe5be
Source dataset
uspto-grants-1981_06
Patent number
US04276295

Reaction notes

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