Water → 3-phenyl-3,4-dihydro-2H-1,4-benzoxazine

HRID 1279682Notes

Reaction equation

HRID 1279682 reaction equation
[C:1]1([C:7]2[CH2:8][O:9][C:10]3[CH:16]=[CH:15][CH:14]=[CH:13][C:11]=3[N:12]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[BH4-].[Na+].O>C(O)C>[C:1]1([CH:7]2[NH:12][C:11]3[CH:13]=[CH:14][CH:15]=[CH:16][C:10]=3[O:9][CH2:8]2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

5

Reactant 3

HCID 962WaterHCID 14817833-phenyl-2H-1,4-benzoxazineHCID 4311764Sodium borohydride

Product 1

HCID 124745723-phenyl-3,4-dihydro-2H-1,4-benzoxazineYield 93%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
90 °C

Procedure

To a slurry of 3-phenyl-2H-1,4-benzoxazine (17 g, 81.2 mmol) in 100 mL absolute ethanol is added sodium borohydride (6.07 g, 162.4 mmol) and water (25 mL). The mixture is heated at 90° C. for 2 h. The mixture is cooled and concentrated, then partitioned between CH2C2 and water. The organic layer is washed twice with water (200 mL), dried over magnesium sulfate and concentrated. The resulting oil is dried under high vacuum to give 15.95 g (93%) of 3-phenyl-3,4-dihydro-2H-1,4-benzoxazine.

Workup

  1. temperatureThe mixture is cooled
  2. concentrationconcentrated
  3. custompartitioned between CH2C2 and water
  4. washThe organic layer is washed twice with water (200 mL)
  5. dry with materialdried over magnesium sulfate
  6. concentrationconcentrated
  7. customThe resulting oil is dried under high vacuum

Sources & evidence

ORD record
ord-17a8f39a166548f79e305f62776fdc7a
Source dataset
uspto-grants-2002_09
Patent number
US06448397B1

Reaction notes

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