HCID 15614948, compound → HCID 15614970, compound

HRID 620363Notes

Reaction equation

HRID 620363 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][CH2:32][CH3:33])=[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][CH2:32][CH3:33])=[O:30])[CH2:21][C:22]([OH:24])=[O:23])=[O:19]

Participants

4

Reactant 1

HCID 15614948HCID 15614948, compound

Product 1

HCID 15614970HCID 15614970, compoundYield 85%

Reagents, catalysts & solvents 2

HCID 284Formic AcidSolventHCID 962WaterSolvent2×

Procedure

A suspension of N-[[2-chloro-6-methoxy-5-(trifluoromethyl)-1-naphthalenyl]carbonyl]-N-(ethoxycarbonyl)glycine, 1,1-dimethylethyl ester (3.13 g, 6.39 mmol) in formic acid (120 mL) was stirred for 3 hours at room temperature under a dry nitrogen atmosphere. Dissolution occurred after an hour. The reaction mixture was diluted with water (1.5 L) and extracted with ether. The extracts were combined, washed well with water and concentrated to leave an oil. The oil was diluted with water and extracted with chloroform. The extracts were combined, dried over magnesium sulfate, filtered and concentrated. The crude solid was recrystallized from benzene:petroleum ether and dried overnight at 90° C. in vacuo to give the title compound as a white solid (2.31 g, 85%), m.p. 144°-146° C.

Workup

  1. dissolutionDissolution
  2. waitoccurred after an hour
  3. extractionextracted with ether
  4. washwashed well with water
  5. concentrationconcentrated
  6. customto leave an oil
  7. extractionextracted with chloroform
  8. dry with materialdried over magnesium sulfate
  9. filtrationfiltered
  10. concentrationconcentrated
  11. customThe crude solid was recrystallized from benzene
  12. dry with materialpetroleum ether and dried overnight at 90° C. in vacuo

Sources & evidence

ORD record
ord-4dd6929f85894fc5976d738b4f70576b
Source dataset
uspto-grants-1989_04
Patent number
US04820727

Reaction notes

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