Ammonium Chloride → 3-amino-6,7,8,9-tetrahydro-5H-benzo[7]annulen-5-one

HRID 2299650Notes

Reaction equation

HRID 2299650 reaction equation
[N+:1]([C:4]1[CH:15]=[CH:14][C:7]2[CH2:8][CH2:9][CH2:10][CH2:11][C:12](=[O:13])[C:6]=2[CH:5]=1)([O-])=O.[Cl-].[NH4+]>C(O)C.O.[Fe]>[NH2:1][C:4]1[CH:15]=[CH:14][C:7]2[CH2:8][CH2:9][CH2:10][CH2:11][C:12](=[O:13])[C:6]=2[CH:5]=1

Participants

6

Reactant 2

HCID 25517Ammonium ChlorideHCID 3444873-Nitro-6,7,8,9-tetrahydro-5H-benzo[a]cyclohepten-5-one

Product 1

HCID 2668073-amino-6,7,8,9-tetrahydro-5H-benzo[7]annulen-5-oneYield 101.3%

Reagents, catalysts & solvents 3

HCID 23925IronCatalystHCID 702EthanolSolventHCID 962WaterSolvent

Procedure

A mixture of 3-nitro-6,7,8,9-tetrahydrobenzocyclohepten-5-one (14.87 g), iron (14.87 g) and ammonium chloride (2.0 g) in ethanol (200 ml) and water (40 ml) was refluxed for 5 hours, and filtered. The filtrate was evaporated in vacuo to afford 3-amino-6,7,8,9-tetrahydrobenzocyclohepten-5-one (12.86 g).

Workup

  1. temperaturewas refluxed for 5 hours
  2. filtrationfiltered
  3. customThe filtrate was evaporated in vacuo

Sources & evidence

ORD record
ord-74352120558a48d49f1648b44b17d620
Source dataset
uspto-grants-2002_12
Patent number
US06495546B1

Reaction notes

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