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

HRID 329379Notes

Reaction equation

HRID 329379 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:14][CH2:13][C:12]2[CH:15]=[CH:16][C:17]([N+:19]([O-])=O)=[CH:18][C:11]=2[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].CO>C(O)C.[Pd]>[NH2:19][C:17]1[CH:16]=[CH:15][C:12]2[CH2:13][CH2:14][N:8]([C:6]([O:5][C:1]([CH3:2])([CH3:4])[CH3:3])=[O:7])[CH2:9][CH2:10][C:11]=2[CH:18]=1

Participants

5

Reactant 2

HCID 887MethanolHCID 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)-carboxylate

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A solution of 3-tertiary-butoxycarbonyl-7-nitro-1,2,4,5-tetrahydro-3H-3-benzazepine (2.1 g) was stirred under a hydrogen atmosphere (50 p.s.i. equivalent to 344.7 kPa) in ethanol (20 ml) and methanol (20 ml) solution containing 5% Pd/C (0.21 g) for 3 hours. The catalyst was removed by filtration and the solvent evaporated to give the title compound as an oil, yield 2.0 g.

Workup

  1. customThe catalyst was removed by filtration
  2. customthe solvent evaporated

Sources & evidence

ORD record
ord-fe478a9825774a46bec3a5a0932b8642
Source dataset
uspto-grants-1990_01
Patent number
US04891372

Reaction notes

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