1-methyl-7-nitro-4,5-dihydro-3,1-benzoxazepin-2(1H)-one → 7-amino-1-methyl-4,5-dihydro-3,1-benzoxazepin-2(1H)-one

HRID 1041717Notes

Reaction equation

HRID 1041717 reaction equation
[N+:1]([C:4]1[CH:5]=[CH:6][C:7]2[N:13]([CH3:14])[C:12](=[O:15])[O:11][CH2:10][CH2:9][C:8]=2[CH:16]=1)([O-])=O>C(O)C.[Ni]>[NH2:1][C:4]1[CH:5]=[CH:6][C:7]2[N:13]([CH3:14])[C:12](=[O:15])[O:11][CH2:10][CH2:9][C:8]=2[CH:16]=1

Participants

4

Reactant 1

HCID 580154381-methyl-7-nitro-4,5-dihydro-3,1-benzoxazepin-2(1H)-one

Product 1

HCID 580154687-amino-1-methyl-4,5-dihydro-3,1-benzoxazepin-2(1H)-one

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 702EthanolSolvent

Procedure

A mixture of 2-nitro-5-methyl-8,9-dihydro-5H-7-oxa-5-aza-benzocyclohepten-6-one (0.7 g) and 50% Raney Ni (1 mL) in ethanol (25 mL) was hydrogenated at 30 psi for 3 hours. The reaction mixture was filtered through celite and concentrated to yield 2-amino-5-methyl-8,9-dihydro-5H-7-oxa-5-aza-benzocyclohepten-6-one: 1H NMR (300 MHz, CDCl3) δ 6.94 (d, 1H), 6.60 (dd, 1H), 6.53 (d, 1H), 4.45 (t, 2H), 3.67 (bs, 1H), 3.33 (s, 3H), 2.87 (t, 2H).

Workup

  1. filtrationThe reaction mixture was filtered through celite and
  2. concentrationconcentrated

Sources & evidence

ORD record
ord-071e93917b264597aed37ad523caffb1
Source dataset
uspto-grants-2013_10
Patent number
US08552186B2

Reaction notes

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