1-Acetylcyclohexene → 3-Amino-4a,5,6,7,8,8a-hexahydro-4H-naphthalen-1-one

HRID 1817809

Reaction equation

CN(C)[C:3]1[CH:8]=[CH:7][C:6]([CH:9]2[CH2:14][C:13](=[O:15])[CH2:12][C:11](=O)[CH2:10]2)=CC=1.C1(C(=O)C)CCCCC=1.C([O-])(=O)C.[NH4+:31]>>[NH2:31][C:11]1[CH2:10][CH:9]2[CH:14]([CH2:3][CH2:8][CH2:7][CH2:6]2)[C:13](=[O:15])[CH:12]=1

Participants

Reactant 3

HCID 136121-Acetylcyclohexene

HCID 517165Ammonium Acetate

HCID 7301175-(4-(Dimethylamino)phenyl)-1,3-cyclohexanedione

Product 1

HCID 578833273-Amino-4a,5,6,7,8,8a-hexahydro-4H-naphthalen-1-one

Procedure

In analogy to (Baraldi, P. G.; Simoni, D.; Manfredini, S.; Synthesis 1983, (11) 902-903) hexahydro-naphthalene-1,3-dione (prepared from 1-cyclohex-1-enyl-ethanone according to (Chuang; Tien. Chem. Ber. 1936; 69; 25-29) was reacted with ammonium acetate to give the title compound as a colorless solid.

Sources & evidence

ORD record: ord-8bf160331b8c4914824225b871c6041a
Source dataset: uspto-grants-2009_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07598384B2

Linked notes

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