HCID 15614944, compound → HCID 3012981, compound

HRID 620354Notes

Reaction equation

HRID 620354 reaction equation
[Cl:1][C:2]1[CH:11]=[CH:10][C:9]2[C:4](=[CH:5][CH:6]=[C:7]([O:16][CH3:17])[C:8]=2[C:12]([F:15])([F:14])[F:13])[C:3]=1[C:18]([N:20]([C:29]([O:31][CH3:32])=[O:30])[CH2:21][C:22]([O:24]C(C)(C)C)=[O:23])=[O:19]>C(O)=O.O>[Cl:1][C:2]1[CH:11]=[CH:10][C:9]2[C:4](=[CH:5][CH:6]=[C:7]([O:16][CH3:17])[C:8]=2[C:12]([F:15])([F:13])[F:14])[C:3]=1[C:18]([N:20]([C:29]([O:31][CH3:32])=[O:30])[CH2:21][C:22]([OH:24])=[O:23])=[O:19]

Participants

4

Reactant 1

HCID 15614944HCID 15614944, compound

Product 1

HCID 3012981HCID 3012981, compoundYield 64.4%

Reagents, catalysts & solvents 2

HCID 284Formic AcidSolventHCID 962WaterSolvent

Procedure

N-[[2-Chloro-6-methoxy-5-(trifluoromethyl)-1-naphthalenyl]carbonyl]-N-(methoxycarbonyl)glycine, 1,1-dimethylethyl ester (3.10 g, 6.51 mmol) was suspended in formic acid (122 mL) under nitrogen at room temperature and stirred for 11/2 hours. The reaction mixture was diluted with water (11/2 L) and extracted with ether (2×200 mL). The extracts were combined, dried over magnesium sulfate and concentrated. The residue was recrystallized from benzene to afford the title compound as a white solid (1.76 g, 64%), m.p. 162°-165° C.

Workup

  1. extractionextracted with ether (2×200 mL)
  2. dry with materialdried over magnesium sulfate
  3. concentrationconcentrated
  4. customThe residue was recrystallized from benzene

Sources & evidence

ORD record
ord-3f5e94b6df2b4e1da0f60c6e08688170
Source dataset
uspto-grants-1989_04
Patent number
US04820727

Reaction notes

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