Methyl iodide → 2,2,4-trimethyl-6-nitro-2H-1,4-benzoxazin-3(4H)-one

HRID 887550Notes

Reaction equation

HRID 887550 reaction equation
[CH3:1][C:2]1([CH3:16])[C:7](=[O:8])[NH:6][C:5]2[CH:9]=[C:10]([N+:13]([O-:15])=[O:14])[CH:11]=[CH:12][C:4]=2[O:3]1.CI.[C:19]([O-])([O-])=O.[K+].[K+]>CN(C=O)C>[CH3:1][C:2]1([CH3:16])[C:7](=[O:8])[N:6]([CH3:19])[C:5]2[CH:9]=[C:10]([N+:13]([O-:15])=[O:14])[CH:11]=[CH:12][C:4]=2[O:3]1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 106566312,2-Dimethyl-6-nitro-2H-benzo[B][1,4]oxazin-3(4H)-one

Product 1

HCID 136655432,2,4-trimethyl-6-nitro-2H-1,4-benzoxazin-3(4H)-one

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

2,2-Dimethyl-6-nitro-4H-benzo[1,4]oxazin-3-one (1.1 g) was mixed with MeI (850 mg, Aldrich), K2CO3 (1.38 g, Aldrich) and DMF (30 ml, Aldrich) at 40° C. for 48 h. The DMF was removed in vacuo and the residue was diluted with EtOAc (80 ml). The organic phase was washed with H2O (50 ml), aqueous Na2SO3 (50 ml) and brine (50 ml). The resulting solution was dried (MgSO4) and concentrated to provide the compound which was used as is for the next reaction step.

Workup

  1. customThe DMF was removed in vacuo
  2. additionthe residue was diluted with EtOAc (80 ml)
  3. washThe organic phase was washed with H2O (50 ml), aqueous Na2SO3 (50 ml) and brine (50 ml)
  4. dry with materialThe resulting solution was dried (MgSO4)
  5. concentrationconcentrated
  6. customto provide the compound which
  7. customas is for the next reaction step

Sources & evidence

ORD record
ord-dc37ecda0d76486c8224f3e43c0b5add
Source dataset
uspto-grants-2012_08
Patent number
US08247430B2

Reaction notes

Loading…