Hydrochloric Acid → 2,2-Dimethyl-6-nitro-3,4-dihydro-2H-benzo[B][1,4]oxazine

HRID 889967Notes

Reaction equation

HRID 889967 reaction equation
[CH3:1][C:2]1([CH3:16])[C:7](=O)[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.Cl>C1COCC1.CO>[CH3:1][C:2]1([CH3:16])[CH2:7][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

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 106566312,2-Dimethyl-6-nitro-2H-benzo[B][1,4]oxazin-3(4H)-one

Product 1

HCID 107270572,2-Dimethyl-6-nitro-3,4-dihydro-2H-benzo[B][1,4]oxazine

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

2,2-Dimethyl-6-nitro-4H-benzo[1,4]oxazin-3-one was added to BH3-THF complex (Aldrich) in THF with ice cooling. The mixture was heated to reflux for 2 h then carefully diluted with 12 mL of MeOH and heated to reflux for an additional 1 h. Concentrated HCl (12 mL) was added and heated to reflux for 1 h. The mixture was concentrated and the resulting solid was suspended in a dilute aqueous solution of NaOH (1 M) and extracted with EtOAc (100 mL×4). The organic layers were washed with H2O and dried over MgSO4. Evaporation of solvent gave a yellow solid.

Workup

  1. temperatureThe mixture was heated
  2. temperatureto reflux for 2 h
  3. temperatureheated
  4. temperatureto reflux for an additional 1 h
  5. temperatureheated
  6. temperatureto reflux for 1 h
  7. concentrationThe mixture was concentrated
  8. extractionextracted with EtOAc (100 mL×4)
  9. washThe organic layers were washed with H2O
  10. dry with materialdried over MgSO4
  11. customEvaporation of solvent
  12. customgave a yellow solid

Sources & evidence

ORD record
ord-f6f984b4e9ba4e95a01a67ada81b7af2
Source dataset
uspto-grants-2006_02
Patent number
US06995162B2

Reaction notes

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