Hydrazine hydrate (1:1) → 1022959-73-4

HRID 1686946Notes

Reaction equation

HRID 1686946 reaction equation
[CH3:1][N:2]1[CH2:8][CH2:7][CH2:6][CH2:5][C:4]2[CH:9]=[C:10]([N+:13]([O-])=O)[CH:11]=[CH:12][C:3]1=2.O.NN>[Pd].C(O)C>[CH3:1][N:2]1[CH2:8][CH2:7][CH2:6][CH2:5][C:4]2[CH:9]=[C:10]([NH2:13])[CH:11]=[CH:12][C:3]1=2

Participants

5

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 672643011-Methyl-7-nitro-2,3,4,5-tetrahydro-1H-benzo[b]azepine

Product 1

HCID 672652741022959-73-4Yield 96%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Conditions

Temperature
60 °C

Procedure

1-Methyl-7-nitro-2,3,4,5-tetrahydro-1H-benzo[b]azepine (135 mg, 0.66 mmol) in a solution of ethanol (4 mL) and hydrazine hydrate (1 mL) was treated with 10% palladium on carbon (40 mg) and heated at 60° C. for 2 h. The mixture was cooled to room temperature, filtered and concentrated to give 1-Methyl-2,3,4,5-tetrahydro-1H-benzo[b]azepin-7-ylamine (110 mgs, 96%) as a grayish oil. 1H-NMR (CDCl3) δ 6.78-6.72 (m, 1H), 6.51 (s, 2H), 3.38 (br s, 2H), 2.82-2.74 (m, 7H), 2.21-2.15 (m, 2H), 1.75-1.68 (m, 2H), 1.57-1.52 (m, 2H); LC/MS (ESI+): 177.16 (M+H).

Workup

  1. temperatureThe mixture was cooled to room temperature
  2. filtrationfiltered
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-fa63f042e606402395407c3148c36665
Source dataset
uspto-grants-2012_04
Patent number
US08148391B2

Reaction notes

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