Ethyl Acetate → 6-Chloro-4-cyclopropyl-7-fluoro-1-hydroxy-1,4-dihydro-quinoxaline-2,3-dione

HRID 1025829Notes

Reaction equation

HRID 1025829 reaction equation
C[O:2][C:3](=O)[C:4]([N:6]([C:10]1[CH:15]=[C:14]([Cl:16])[C:13]([F:17])=[CH:12][C:11]=1[N+:18]([O-:20])=O)[CH:7]1[CH2:9][CH2:8]1)=[O:5].C(OCC)(=O)C>CO>[Cl:16][C:14]1[CH:15]=[C:10]2[C:11](=[CH:12][C:13]=1[F:17])[N:18]([OH:20])[C:3](=[O:2])[C:4](=[O:5])[N:6]2[CH:7]1[CH2:9][CH2:8]1

Participants

4

Reactant 2

HCID 8857Ethyl AcetateHCID 67320260N-(5-chloro-4-fluoro-2-nitro-phenyl)-N-cyclopropyl-oxalamic acid methyl ester

Product 1

HCID 673202126-Chloro-4-cyclopropyl-7-fluoro-1-hydroxy-1,4-dihydro-quinoxaline-2,3-dione

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 1.2 g (3.789 mmol) N-(5-chloro-4-fluoro-2-nitro-phenyl)-N-cyclopropyl-oxalamic acid methyl ester in 15 mL MeOH was added 120 mg Pd(C) 10% on charcoal. The reaction mixture was stirred for 2 hours under hydrogen atmosphere at 1.2 bar at room temperature. 30 mL ethyl acetate was added and the reaction mixture was filtered over Dicalite® speed plus (Acros) speed plus (Acros) and concentrated under vacuum. Light yellow solid (68%). MS (ESI): m/z=269.014 [M+H]+.

Workup

  1. filtrationthe reaction mixture was filtered over Dicalite® speed plus (Acros) speed plus (Acros)
  2. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-e2ac76cfde644f1ba5f9b36c1275b35e
Source dataset
uspto-grants-2014_05
Patent number
US08729091B2

Reaction notes

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