Hydrochloric Acid → HCID 11185063, compound

HRID 1680831Notes

Reaction equation

HRID 1680831 reaction equation
[NH2:1][C:2]1[CH:10]=[C:9]([CH3:11])[C:8]([C:12]([O:14][CH2:15][CH3:16])=[O:13])=[C:7]([CH3:17])[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[CH:10]=[C:9]([CH3:11])[C:8]([C:12]([O:14][CH2:15][CH3:16])=[O:13])=[C:7]([CH3:17])[C:3]=1[C:4]([OH:6])=[O:5])(=[O:26])[CH3:25]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 1049PyridineHCID 6367Acetyl chlorideHCID 126858402-Amino-5-ethoxycarbonyl-4,6-dimethylbenzoic acid

Product 1

HCID 11185063HCID 11185063, compoundYield 86.6%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent2×

Procedure

To a mixture consisting of 1 g of 2-amino-5-ethoxycarbonyl-4,6-dimethylbenzoic acid, 20 ml of benzene, and 0.7 ml of pyridine in a flask cooled with ice water was added dropwise with stirring a solution of 600 mg of acetyl chloride in 5 ml of benzene. The mixture was further stirred for 5 hours at room temperature, and then heated to reflux for one hour. After cooling, the mixture was shaken with dilute hydrochloric acid and 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 resulting residue was recrystallized from ethanol/water to yield 1.02 g of 2-acetylamino-5-ethoxycarbonyl-4,6-dimethylbenzoic acid melting at 170°-171° C.

Workup

  1. additionwas added dropwise
  2. temperatureheated
  3. temperatureto reflux for one hour
  4. temperatureAfter cooling
  5. customthe layers were separated
  6. extractionThe acidic aqueous layer was extracted with ethyl acetate
  7. washthe combined organic extracts were washed with water
  8. dry with materialdried over sodium sulfate
  9. customThe solvent was removed by distillation
  10. customThe resulting residue was recrystallized from ethanol/water

Sources & evidence

ORD record
ord-93fbbec4f8b44f7f9073021acd3c7396
Source dataset
uspto-grants-1981_06
Patent number
US04276295

Reaction notes

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