3-Ethyl-7-nitro-2,3,4,5-tetrahydro-1H-benzo[d]azepine → 3-Ethyl-2,3,4,5-tetrahydro-1H-benzo[d]azepin-7-ylamine

HRID 1686905Notes

Reaction equation

HRID 1686905 reaction equation
[CH2:1]([N:3]1[CH2:9][CH2:8][C:7]2[CH:10]=[C:11]([N+:14]([O-])=O)[CH:12]=[CH:13][C:6]=2[CH2:5][CH2:4]1)[CH3:2].[H][H]>CO.[Pd]>[CH2:1]([N:3]1[CH2:9][CH2:8][C:7]2[CH:10]=[C:11]([NH2:14])[CH:12]=[CH:13][C:6]=2[CH2:5][CH2:4]1)[CH3:2]

Participants

5

Reactant 2

HCID 189435263-Ethyl-7-nitro-2,3,4,5-tetrahydro-1H-benzo[d]azepineHCID 178418361HCID 178418361, compound

Product 1

HCID 189434013-Ethyl-2,3,4,5-tetrahydro-1H-benzo[d]azepin-7-ylamine

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent2×

Procedure

3-Ethyl-7-nitro-2,3,4,5-tetrahydro-1H-benzo[d]azepine (740 mg/3.4 mmol) was dissolved in anhydrous methanol (ca. 10 mL) and the solution added to a Parr flask. Palladium (10% on charcoal) was added carefully (WARNING: this addition should be done under a atmosphere of nitrogen to avoid ignition of methanol vapor in flask) and the mixture shaken under 40 psi of hydrogen for 2 hours. The mixture was then filtered and the colorless filtrate concentrated to afford 3-Ethyl-2,3,4,5-tetrahydro-1H-benzo [d]azepin-7-ylamine (yellows upon standing). The material was typically used without further purification (680 mg/quantitative). 1H NMR (400 MHz, CDCl3) δ 6.9 (d, J=7.6 Hz, 1H), 6.4 (m, 2H), 2.9 (m, 4H), 2.7 (m, 6H), 1.1 (t, J=7.1 Hz, 3H).

Workup

  1. additionthe solution added to a Parr flask
  2. additionthis addition
  3. filtrationThe mixture was then filtered
  4. concentrationthe colorless filtrate concentrated

Sources & evidence

ORD record
ord-d1cc969161904d7390466c4e9967e30e
Source dataset
uspto-grants-2012_04
Patent number
US08148391B2

Reaction notes

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