Acetic Anhydride → 1-(6-nitro-2H-benzo[b][1,4]oxazin-4(3H)-yl)ethanone

HRID 1618593Notes

Reaction equation

HRID 1618593 reaction equation
[N+:1]([C:4]1[CH:13]=[CH:12][C:7]2[O:8][CH2:9][CH2:10][NH:11][C:6]=2[CH:5]=1)([O-:3])=[O:2].[C:14](OC(=O)C)(=[O:16])[CH3:15]>CCOC(C)=O>[N+:1]([C:4]1[CH:13]=[CH:12][C:7]2[O:8][CH2:9][CH2:10][N:11]([C:14](=[O:16])[CH3:15])[C:6]=2[CH:5]=1)([O-:3])=[O:2]

Participants

4

Reactant 2

HCID 7918Acetic AnhydrideHCID 70622256-nitro-3,4-dihydro-2H-1,4-benzoxazine

Product 1

HCID 578647141-(6-nitro-2H-benzo[b][1,4]oxazin-4(3H)-yl)ethanone

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

A solution of 6-nitro-3,4-dihydro-2H-benzo[b][1,4]oxazine (0.7 g, 3.89 mmol) in acetic anhydride (1.9 mL) and EtOAc (7 mL) was heater under reflux with stirring. After 15 h, the mixture was concentrated under reduced pressure to give 1-(6-nitro-2H-benzo[b][1,4]oxazin-4(3H)-yl)ethanone as a yellow solid, which was carried on crude without purification: Mass Spectrum (ESI) m/e=223.0 (M+1).

Workup

  1. temperatureunder reflux
  2. concentrationthe mixture was concentrated under reduced pressure

Sources & evidence

ORD record
ord-edad656934fe4b6ab0cb1d840dfd2b9b
Source dataset
uspto-grants-2014_07
Patent number
US08765940B2

Reaction notes

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