Sodium Hydroxide → 7-Bromo-3,4-dihydro-2H-1,4-benzoxazine

HRID 987527Notes

Reaction equation

HRID 987527 reaction equation
C([N:4]1[C:9]2[CH:10]=[CH:11][C:12]([Br:14])=[CH:13][C:8]=2[O:7][CH2:6][CH2:5]1)(=O)C.[OH-].[Na+]>CO>[Br:14][C:12]1[CH:11]=[CH:10][C:9]2[NH:4][CH2:5][CH2:6][O:7][C:8]=2[CH:13]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 180089591-(7-Bromo-2,3-dihydro-4H-1,4-benzoxazin-4-yl)ethan-1-one

Product 1

HCID 180089607-Bromo-3,4-dihydro-2H-1,4-benzoxazineYield 75.6%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
50 °C

Procedure

A solution of 4-acetyl-7-bromo-3,4-dihydro-2H-benzo[1,4]oxazine (9.5 g, Reference Example 13) in methanol (200 ml) was treated with aqueous sodium hydroxide (50 ml, 3M) was stirred at 50° C. for 2 hours. The mixture was evaporated to low bulk, then diluted with water (100 ml) and then extracted three times with dichloromethane (200 ml). The combined extracts were dried over magnesium sulphate then evaporated to give the title compound (6.0 g) as a brown oil.

Workup

  1. customThe mixture was evaporated to low bulk
  2. additiondiluted with water (100 ml)
  3. extractionextracted three times with dichloromethane (200 ml)
  4. dry with materialThe combined extracts were dried over magnesium sulphate
  5. customthen evaporated

Sources & evidence

ORD record
ord-77ec34ed31dd4cd595917c5beb1addc9
Source dataset
uspto-grants-2003_10
Patent number
US06632814B1

Reaction notes

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