Hydrochloric Acid → 5-Acetyl-2-acetylamino-4-trifluoromethyl-benzoic acid methyl ester

HRID 906504Notes

Reaction equation

HRID 906504 reaction equation
[CH3:1][O:2][C:3](=[O:23])[C:4]1[CH:9]=[C:8]([C:10]([O:12]CC)=[CH2:11])[C:7]([C:15]([F:18])([F:17])[F:16])=[CH:6][C:5]=1[NH:19][C:20](=[O:22])[CH3:21].Cl.CCOC(C)=O>C1COCC1>[CH3:1][O:2][C:3](=[O:23])[C:4]1[CH:9]=[C:8]([C:10](=[O:12])[CH3:11])[C:7]([C:15]([F:18])([F:17])[F:16])=[CH:6][C:5]=1[NH:19][C:20](=[O:22])[CH3:21]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 8857Ethyl AcetateHCID 59164443HCID 59164443, compound

Product 1

HCID 591644065-Acetyl-2-acetylamino-4-trifluoromethyl-benzoic acid methyl esterYield 76%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of crude 2-acetylamino-5-(1-ethoxy-vinyl)-4-trifluoromethyl-benzoic acid methyl ester from above in THF (100 mL) was treated with aqueous hydrochloric acid (1N, 50 mL), and the mixture was stirred at r.t. for 1 h under nitrogen. The mixture was then poured into EtOAc and washed once with water. The organic phase was dried over anhydrous sodium sulfate, filtered and concentrated in vacuo. The crude product was purified by column chromatography (silica gel 60, hexanes/EtOAc 2:1) to give 5-acetyl-2-acetylamino-4-trifluoromethyl-benzoic acid methyl ester (10.7 g, 35.1 mmol, 76% over two steps) as a white powder, m.p. 66-69° C., ESI-MS: m/z 326 [M+Na]+.

Workup

  1. washwashed once with water
  2. dry with materialThe organic phase was dried over anhydrous sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customThe crude product was purified by column chromatography (silica gel 60, hexanes/EtOAc 2:1)

Sources & evidence

ORD record
ord-d78277f9165847399df9cb665e15036e
Source dataset
uspto-grants-2011_09
Patent number
US08012988B2

Reaction notes

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