Water → 3-amino-5,5-dimethyl-8-nitro-3,4-dihydro-1H-1-benzazepin-2-one

HRID 1687635Notes

Reaction equation

HRID 1687635 reaction equation
[N:1]([CH:4]1[CH2:10][C:9]([CH3:12])([CH3:11])[C:8]2[CH:13]=[CH:14][C:15]([N+:17]([O-:19])=[O:18])=[CH:16][C:7]=2[NH:6][C:5]1=[O:20])=[N+]=[N-].C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1COCC1.O>>[NH2:1][CH:4]1[CH2:10][C:9]([CH3:12])([CH3:11])[C:8]2[CH:13]=[CH:14][C:15]([N+:17]([O-:19])=[O:18])=[CH:16][C:7]=2[NH:6][C:5]1=[O:20]

Participants

5

Reactant 4

HCID 962WaterHCID 8028TetrahydrofuranHCID 11776TriphenylphosphineHCID 866339913-Azido-5,5-dimethyl-8-nitro-1,3,4,5-tetrahydro-1-benzazepin-2-one

Product 1

HCID 672640283-amino-5,5-dimethyl-8-nitro-3,4-dihydro-1H-1-benzazepin-2-one

Procedure

3-Azido-5,5-dimethyl-8-nitro-1,3,4,5-tetrahydro-1-benzazepin-2-one (3.10 g, 10.3 mmol), Triphenylphosphine Resin (12 g, 11.55 mmol), THF (120 mL, 1400 mmol) and Water (0.9 mL, 50 mmol) were combined and stirred at rt for 16 h. The reaction mixture was filtered. Product isolated as a beige solid. (HPLC purity >98%)

Workup

  1. filtrationThe reaction mixture was filtered
  2. customProduct isolated as a beige solid

Sources & evidence

ORD record
ord-8fc24e76ef6f4f5280ec1040d7145a45
Source dataset
uspto-grants-2012_04
Patent number
US08148391B2

Reaction notes

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