7-Methyl-3,4-dihydro-2H-1,4-benzoxazine → HCID 86691924, compound

HRID 717763Notes

Reaction equation

HRID 717763 reaction equation
[CH3:1][C:2]1[CH:3]=[CH:4][C:5]2[NH:10][CH2:9][CH2:8][O:7][C:6]=2[CH:11]=1.[N:12]([O-])=[O:13].[Na+]>Cl.O>[CH3:1][C:2]1[CH:3]=[CH:4][C:5]2[N:10]([N:12]=[O:13])[CH2:9][CH2:8][O:7][C:6]=2[CH:11]=1

Participants

5

Reactant 2

HCID 125105457-Methyl-3,4-dihydro-2H-1,4-benzoxazineHCID 23668193Sodium Nitrite

Product 1

HCID 86691924HCID 86691924, compoundYield 81%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 962WaterSolvent2×

Procedure

3,4-Dihydro-7-methyl-2H-benzo[b][1,4]oxazine (280 mg, 1.87 mmol) was dissolved in 3N HCl (20 mL). Sodium nitrite (129 mg, 1.87 mmol) in water (1 mL) was added dropwise into the reaction mixture at 0° C. The reaction mixture was stirred for 2 h at RT. The reaction mixture was diluted with water (20 mL) and extracted with EtOAc. The organic layer was dried over sodium sulfate and concentrated under vacuum to obtain 270 mg of 7-Methyl-4-nitroso-3,4-dihydro-2H-benzo[1,4]oxazine (free base).

Workup

  1. extractionextracted with EtOAc
  2. dry with materialThe organic layer was dried over sodium sulfate
  3. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-86d472223d884c06a141ef1efab5af52
Source dataset
uspto-grants-2015_11
Patent number
US09193728B2

Reaction notes

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