2,2-dimethyl-3,4-dihydro-2H-1,4-benzoxazin-3-one → 2,2-dimethyl-3,4-dihydro-2H-1,4-benzoxazine

HRID 72563Notes

Reaction equation

HRID 72563 reaction equation
[H-].[H-].[H-].[H-].[Li+].[Al+3].[CH3:7][C:8]1([CH3:19])[C:13](=O)[NH:12][C:11]2[CH:15]=[CH:16][CH:17]=[CH:18][C:10]=2[O:9]1>C1COCC1>[CH3:7][C:8]1([CH3:19])[CH2:13][NH:12][C:11]2[CH:15]=[CH:16][CH:17]=[CH:18][C:10]=2[O:9]1

Participants

4

Reactant 2

HCID 106073952,2-dimethyl-3,4-dihydro-2H-1,4-benzoxazin-3-oneHCID 21226445Aluminium lithium hydride

Product 1

HCID 235871012,2-dimethyl-3,4-dihydro-2H-1,4-benzoxazineYield 94.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
25 °C

Procedure

To a stirred solution of LAH (3.01 g, 79.10 mmol) in THF (80 mL) at 0° C. was added 2,2-dimethyl-4H-benzo[1,4]oxazin-3-one (7.00 g, 39.5 mmol) in portions and stirred the reaction mixture at 25° C. for 1 h and then 50° C. for 3 h. Reaction mixture was quenched by the addition cold saturated sodium sulfate solution and it was filtered through celite and extracted with DCM (100 mL×2), washed with brine (50 mL), dried over sodium sulfate, concentrated to give 2,2-dimethyl-3,4-dihydro-2H-benzo[1,4]oxazine (6.09 g), which was used as such for the next reaction without purification

Workup

  1. wait50° C. for 3 h
  2. customReaction mixture
  3. customwas quenched by the addition cold saturated sodium sulfate solution and it
  4. filtrationwas filtered through celite
  5. extractionextracted with DCM (100 mL×2)
  6. washwashed with brine (50 mL)
  7. dry with materialdried over sodium sulfate
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-53fcbe77a24f45bd8668df6b2f1da170
Source dataset
uspto-grants-2014_09
Patent number
US08828951B2

Reaction notes

Loading…