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

HRID 1644367Notes

Reaction equation

HRID 1644367 reaction equation
C([O:3][C:4](=O)[CH2:5][O:6][C:7]1[CH:12]=[CH:11][C:10]([C:13](=[O:15])[CH3:14])=[CH:9][C:8]=1[N+:16]([O-])=O)C.COC1C=CC2OCC(=O)NC=2C=1>C(O)(=O)C.[Fe]>[C:13]([C:10]1[CH:11]=[CH:12][C:7]2[O:6][CH2:5][C:4](=[O:3])[NH:16][C:8]=2[CH:9]=1)(=[O:15])[CH3:14]

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-c056be5af8ee4101be58ebb686a0dde2
Source dataset
uspto-grants-2012_02
Patent number
US08124602B2

Reaction notes

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