3,4-Dihydro-2H-1,4-benzoxazine → 63169-10-8

HRID 717773Notes

Reaction equation

HRID 717773 reaction equation
[O:1]1[C:6]2[CH:7]=[CH:8][CH:9]=[CH:10][C:5]=2[NH:4][CH2:3][CH2:2]1.[N:11]([O-])=[O:12].[Na+]>Cl.O>[N:11]([N:4]1[CH2:3][CH2:2][O:1][C:6]2[CH:7]=[CH:8][CH:9]=[CH:10][C:5]1=2)=[O:12]

Participants

5

Reactant 2

HCID 5850963,4-Dihydro-2H-1,4-benzoxazineHCID 23668193Sodium Nitrite

Product 1

HCID 2185961163169-10-8Yield 77.4%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 962WaterSolvent2×

Conditions

Temperature
0 °C

Procedure

3,4-Dihydro-2H-benzo[1,4]oxazine (425 mg, 3.148 mmol) was dissolved in HCl (3N) at 0° C., and stirred for 5 min. at 0° C. A solution of sodium nitrite (217 mg, 3.148 mmol) in water was added at the same temperature, and the reaction mixture stirred at 0° C. for 1 h. After completion of reaction, water was added and the mixture extracted with DCM. The combined organic layers were dried over sodium sulfate and concentrated under reduced pressure, to give 400 mg desired product.

Workup

  1. stirringthe reaction mixture stirred at 0° C. for 1 h
  2. additionwas added
  3. extractionthe mixture extracted with DCM
  4. dry with materialThe combined organic layers were dried over sodium sulfate
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-3528499babf147549e375d59ab7f6117
Source dataset
uspto-grants-2015_11
Patent number
US09193728B2

Reaction notes

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