6-methoxy-3,4-dihydro-2H-1,4-benzoxazin-3-one → 6-Acetyl-2H-1,4-benzoxazin-3(4H)-one

HRID 255248Notes

Reaction equation

HRID 255248 reaction equation
[C:1]([C:4]1[CH:16]=[CH:15][C:7]([O:8][CH2:9][C:10](OCC)=[O:11])=[C:6]([N+:17]([O-])=O)[CH:5]=1)(=[O:3])[CH3:2].COC1C=CC2OCC(=O)NC=2C=1>C(O)(=O)C.[Fe]>[C:1]([C:4]1[CH:16]=[CH:15][C:7]2[O:8][CH2:9][C:10](=[O:11])[NH:17][C:6]=2[CH:5]=1)(=[O:3])[CH3:2]

Participants

5

Reactant 2

HCID 132049526-methoxy-3,4-dihydro-2H-1,4-benzoxazin-3-oneHCID 86642623Ethyl (4-acetyl-2-nitrophenoxy)acetate2×

Product 1

HCID 36419566-Acetyl-2H-1,4-benzoxazin-3(4H)-oneYield 51%

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 176Acetic AcidSolvent

Procedure

Ethyl (4-acetyl-2-nitrophenoxy)acetate (Intermediate 90) was reacted with iron in acetic acid as described for Intermediate 48. The crude product was obtained as an off white solid after work up. Recrystallization with ethyl acetate/methanol afforded the product as a colorless solid in 51% yield.

Workup

  1. customThe crude product was obtained as an off white solid after work up
  2. customRecrystallization with ethyl acetate/methanol

Sources & evidence

ORD record
ord-91875a070ac843faa0a2ddd4f5873564
Source dataset
uspto-grants-2011_01
Patent number
US07875715B2

Reaction notes

Loading…