Hydrazine hydrate (1:1) → 7-Amino-1-methyl-1,3,4,5-tetrahydro-benzo[B]azepin-2-one

HRID 1040577Notes

Reaction equation

HRID 1040577 reaction equation
[CH3:1][N:2]1[C:8](=[O:9])[CH2:7][CH2:6][CH2:5][C:4]2[CH:10]=[C:11]([N+:14]([O-])=O)[CH:12]=[CH:13][C:3]1=2.O.NN>C(O)C.[Pd]>[NH2:14][C:11]1[CH:12]=[CH:13][C:3]2[N:2]([CH3:1])[C:8](=[O:9])[CH2:7][CH2:6][CH2:5][C:4]=2[CH:10]=1

Participants

5

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 578538961-Methyl-7-nitro-1,3,4,5-tetrahydrobenzo[b]azepin-2-one

Product 1

HCID 197602587-Amino-1-methyl-1,3,4,5-tetrahydro-benzo[B]azepin-2-one

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

1-Methyl-7-nitro-1,3,4,5-tetrahydrobenzo[b]azepin-2-one (185 mg, 0.84 mmol) was dissolved in ethanol (3.5 ml). 10% palladium on carbon (50 mg) and hydrazine hydrate (1 ml) were then added, and the mixture was heated to reflux for 2 hours. After cooling to room temperature, the mixture was then filtered through Celite and concentrated to give 7-Amino-1-methyl-1,3,4,5-tetrahydrobenzo[b]azepin-2-one as a clear oil, 166 mg. 1H NMR (400 MHz, DMSO-d6) δ 6.92-6.97 (m, 1H), 6.42-6.50 (m, 1H), 6.40 (s, 1H), 5.13 (s, 2H), 3.10 (s, 3H), 1.90-2.16 (m, 6H); MS (m/e) 221 (M+1).

Workup

  1. temperaturethe mixture was heated
  2. temperatureto reflux for 2 hours
  3. filtrationthe mixture was then filtered through Celite
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-bd2f99d624c445e3816da219b34de312
Source dataset
uspto-grants-2013_10
Patent number
US08552186B2

Reaction notes

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