tert-butyl 7-nitro-2,3,4,5-tetrahydro-1H-3-benzazepine-3-carboxylate → Tert-butyl 7-amino-4,5-dihydro-1H-benzo[D]azepine-3(2H)-carboxylate

HRID 1668581Notes

Reaction equation

HRID 1668581 reaction equation
[N+:1]([C:4]1[CH:21]=[CH:20][C:7]2[CH2:8][CH2:9][N:10]([C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])[CH2:11][CH2:12][C:6]=2[CH:5]=1)([O-])=O>CO.[Pd]>[NH2:1][C:4]1[CH:21]=[CH:20][C:7]2[CH2:8][CH2:9][N:10]([C:13]([O:15][C:16]([CH3:17])([CH3:19])[CH3:18])=[O:14])[CH2:11][CH2:12][C:6]=2[CH:5]=1

Participants

4

Reactant 1

HCID 21918821tert-butyl 7-nitro-2,3,4,5-tetrahydro-1H-3-benzazepine-3-carboxylate

Product 1

HCID 11402789Tert-butyl 7-amino-4,5-dihydro-1H-benzo[D]azepine-3(2H)-carboxylateYield 87.4%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

1,1-dimethylethyl 7-nitro-1,2,4,5-tetrahydro-3H-3-benzazepine-3-carboxylate (3.25 g) was hydrogenated for 3 h under atmospheric pressure at 25° C. in the presence of 10% Pd/C (0.32 g) in MeOH (130 ml). The catalyst was removed by filtration, the solvent evaporated under reduced pressure and the resulting residue was purified by flash chromatography over silica gel (eluting with 40% ethyl acetate in hexane) to give the title compound (2.55 g).

Workup

  1. customThe catalyst was removed by filtration
  2. customthe solvent evaporated under reduced pressure
  3. customthe resulting residue was purified by flash chromatography over silica gel (eluting with 40% ethyl acetate in hexane)

Sources & evidence

ORD record
ord-d158ea3df4fc4155b2ed5d7811cf8ad7
Source dataset
uspto-grants-2011_08
Patent number
US07989444B2

Reaction notes

Loading…