4-Nitroso-3-phenyl-3,4-dihydro-2H-1,4-benzoxazine → 3-phenyl-2,3-dihydro4H-1,4-benzoxazin-4-ylamine

HRID 1279684Notes

Reaction equation

HRID 1279684 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[N:7]([N:9]1[C:14]2[CH:15]=[CH:16][CH:17]=[CH:18][C:13]=2[O:12][CH2:11][CH:10]1[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)=O>C(OCC)C>[C:19]1([CH:10]2[N:9]([NH2:7])[C:14]3[CH:15]=[CH:16][CH:17]=[CH:18][C:13]=3[O:12][CH2:11]2)[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=1

Participants

4

Reactant 2

HCID 121486174-Nitroso-3-phenyl-3,4-dihydro-2H-1,4-benzoxazineHCID 21226445Aluminium lithium hydride

Product 1

HCID 121486183-phenyl-2,3-dihydro4H-1,4-benzoxazin-4-ylamineYield 61%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

A slurry of lithium aluminum hydride (4.9 g, 130.5 mmol) in ethyl ether (100 mL) is stirred at ice bath temperature under an argon atmosphere. A solution of 4-nitroso-3-phenyl-3,4-dihydro-2H-1,4-benzoxazine in ethyl ether (300 mL) is added dropwise over 1 h. The mixture is removed from the ice bath and allowed to stir for 18 h. Water (50 mL) is slowly added forming solids. The solids are collected by filtration and washed with ethyl ether. The resulting filtrates are combined and washed three times with water (200 mL), dried over magnesium sulfate, and concentrated to give 8.7g (61%) of 3-phenyl-2,3-dihydro-4H-1,4-benzoxazin-4-ylamine.

Workup

  1. customThe mixture is removed from the ice bath
  2. additionWater (50 mL) is slowly added
  3. customforming solids
  4. filtrationThe solids are collected by filtration
  5. washwashed with ethyl ether
  6. washwashed three times with water (200 mL)
  7. dry with materialdried over magnesium sulfate
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-2b0d98cdf78d4f14895769f59ebb5fce
Source dataset
uspto-grants-2002_09
Patent number
US06448397B1

Reaction notes

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