7-Hydroxy-8-nitro-1,2,4,5-tetrahydro-benzo[d]azepine-3-carboxylic acid tert-butyl ester → 1,1-Dimethylethyl 7-amino-8-hydroxy-1,2,4,5-tetrahydro-3H-3-benzazepine-3-carboxylate

HRID 1668561Notes

Reaction equation

HRID 1668561 reaction equation
[OH:1][C:2]1[C:19]([N+:20]([O-])=O)=[CH:18][C:5]2[CH2:6][CH2:7][N:8]([C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])[CH2:9][CH2:10][C:4]=2[CH:3]=1>CCO.[Pd]>[NH2:20][C:19]1[C:2]([OH:1])=[CH:3][C:4]2[CH2:10][CH2:9][N:8]([C:11]([O:13][C:14]([CH3:16])([CH3:17])[CH3:15])=[O:12])[CH2:7][CH2:6][C:5]=2[CH:18]=1

Participants

4

Reactant 1

HCID 589728117-Hydroxy-8-nitro-1,2,4,5-tetrahydro-benzo[d]azepine-3-carboxylic acid tert-butyl ester

Product 1

HCID 591504721,1-Dimethylethyl 7-amino-8-hydroxy-1,2,4,5-tetrahydro-3H-3-benzazepine-3-carboxylateYield 100%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

1,1-Dimethylethyl 7-hydroxy-8-nitro-1,2,4,5-tetrahydro-3H-3-benzazepine-3-carboxylate (8.2 g) was hydrogenated for 4 h under atmospheric pressure and 25° C. in the presence of 10% Pd/C (1.4 g) in EtOH (200 ml). The catalyst was removed by filtration and volatiles evaporated to provide the title compound as a grey solid (7.4 g).

Workup

  1. customThe catalyst was removed by filtration and volatiles
  2. customevaporated

Sources & evidence

ORD record
ord-8a02e9e50c264216918e111120e3c193
Source dataset
uspto-grants-2011_08
Patent number
US07989444B2

Reaction notes

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