1-(5,5-Dimethyl-8-nitro-2,3,4,5-tetrahydrobenzo[b]azepin-1-yl)ethanone → 1-(8-Amino-2,3,4,5-tetrahydro-5,5-dimethylbenzo[b]azepin-1-yl)ethanone

HRID 1805035Notes

Reaction equation

HRID 1805035 reaction equation
[CH3:1][C:2]1([CH3:19])[CH2:8][CH2:7][CH2:6][N:5]([C:9](=[O:11])[CH3:10])[C:4]2[CH:12]=[C:13]([N+:16]([O-])=O)[CH:14]=[CH:15][C:3]1=2>CO.[Pd]>[NH2:16][C:13]1[CH:14]=[CH:15][C:3]2[C:2]([CH3:19])([CH3:1])[CH2:8][CH2:7][CH2:6][N:5]([C:9](=[O:11])[CH3:10])[C:4]=2[CH:12]=1

Participants

4

Reactant 1

HCID 578647131-(5,5-Dimethyl-8-nitro-2,3,4,5-tetrahydrobenzo[b]azepin-1-yl)ethanone

Product 1

HCID 578647161-(8-Amino-2,3,4,5-tetrahydro-5,5-dimethylbenzo[b]azepin-1-yl)ethanone

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A suspension of 1-(5,5-dimethyl-8-nitro-2,3,4,5-tetrahydrobenzo[b]azepin-1-yl)ethanone (1.05 g, 40 mmol) and 10% Pd—C (0.2 g) in MeOH (20 mL) was stirred under H2 (1 atm) at room temperature for 4 h. After filtration, the filtrate was concentrated to give 1-(8-amino-2,3,4,5-tetrahydro-5,5-dimethylbenzo[b]azepin-1-yl)ethanone as a white solid (DC-4) (880 mg, 94%). 1H NMR (CDCl3) δ 7.06 (d, J=8.0 Hz, 1H), 6.59 (dd, J=8.4, 2.4 Hz, 1H), 6.50 (br s, 1H), 4.18-4.05 (m, 1H), 3.46-3.36 (m, 1H), 2.23 (s, 3H), 1.92-1.85 (m, 1H), 1.61-1.51 (m, 3H), 1.21 (s, 3H), 0.73 (t, J=7.2 Hz, 3H); ESI-MS 233.0 m/z (MH+).

Workup

  1. filtrationAfter filtration
  2. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-4982dc1b0fe14b868b04aa1e348d2511
Source dataset
uspto-grants-2013_01
Patent number
US08354427B2

Reaction notes

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