Sodium borohydride → HCID 43229644, compound

HRID 1914532Notes

Reaction equation

HRID 1914532 reaction equation
[BH4-].[Na+].[Br:3][C:4]1[CH:5]=[C:6]([CH:10]2[NH:15][C:14]3[CH:16]=[CH:17][CH:18]=[CH:19][C:13]=3[CH2:12][O:11]2)[CH:7]=[CH:8][CH:9]=1>C(O)C>[Br:3][C:4]1[CH:5]=[C:6]([CH:7]=[CH:8][CH:9]=1)[CH2:10][NH:15][C:14]1[CH:16]=[CH:17][CH:18]=[CH:19][C:13]=1[CH2:12][OH:11]

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 49780152HCID 49780152, compound

Product 1

HCID 43229644HCID 43229644, compoundYield 86.4%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Under a nitrogen atmosphere, sodium borohydride (0.1172 mol) was added slowly to a mixture of 2-(3-bromo-phenyl)-1,4-dihydro-2H-benzo[d][1,3]oxazine (0.0586 mol) in ethanol (200 mL). The reaction mixture was stirred and refluxed for 1 hour. The mixture was cooled on an ice-water bath, quenched with NH4Cl 20% and extracted with DCM. The organic layer was dried, filtered and the solvent was evaporated, yielding 14.8 g of the desired product.

Workup

  1. temperaturerefluxed for 1 hour
  2. temperatureThe mixture was cooled on an ice-water bath
  3. customquenched with NH4Cl 20%
  4. extractionextracted with DCM
  5. customThe organic layer was dried
  6. filtrationfiltered
  7. customthe solvent was evaporated

Sources & evidence

ORD record
ord-2bcac49f53c84992a4d268c0c4201218
Source dataset
uspto-grants-2013_12
Patent number
US08614201B2

Reaction notes

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