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

HRID 840979Notes

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.O.O.[Sn](Cl)Cl.[OH-].[Na+]>C(O)C>[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

Conditions

Temperature: 70 °C

Procedure

A mixture of 3-nitro-6,7,8,9-tetrahydro-5H-benzocyclohepten-5-one (10.0 g, 48.73 mmol), tin(II) chloride dihydrate (49.48 g, 219.3 mmol) and ethanol (200 ml) was stirred at 70° C. for 2 hours. The reaction mixture was poured into ice water, adjusted to pH 10 with sodium hydroxide, and then extracted with toluene. The extract solution was washed with water and a saturated aqueous sodium chloride solution and dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure and the resulting residue was purified by a silica gel column chromatography (eluent: ethyl acetate/n-hexane=1/2) to obtain 8.08 g of 3-amino-6,7,8,9-tetrahydro-5H-benzocyclohepten-5-one.

Workup

extractionextracted with toluene
washThe extract solution was washed with water
dry with materiala saturated aqueous sodium chloride solution and dried over anhydrous magnesium sulfate
distillationThe solvent was distilled off under reduced pressure
customthe resulting residue was purified by a silica gel column chromatography (eluent: ethyl acetate/n-hexane=1/2)

Sources & evidence

ORD record: ord-74edc409965c465b9d27278514dc866d
Source dataset: uspto-grants-2002_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06369110B1

Reaction notes

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