3-Amino-5,5-dimethyl-2-cyclohexen-1-one → 3,4,6,7,9,10-hexahydro-3,3,6,6-tetramethyl-9-[3-(4-pyridyloxy)-phenyl]-1,8(2H,5H)-acridinedione

HRID 1740435Notes

Reaction equation

HRID 1740435 reaction equation
[NH2:1][C:2]1[CH2:7][C:6]([CH3:9])([CH3:8])[CH2:5][C:4](=[O:10])[CH:3]=1.CO[CH:13](OC)[C:14]1[CH:19]=[CH:18][CH:17]=[C:16]([O:20][C:21]2[CH:26]=[CH:25][N:24]=[CH:23][CH:22]=2)[CH:15]=1>>[CH3:8][C:6]1([CH3:9])[CH2:7][C:2]2[NH:1][C:2]3[CH2:7][C:6]([CH3:9])([CH3:8])[CH2:5][C:4](=[O:10])[C:3]=3[CH:13]([C:14]3[CH:19]=[CH:18][CH:17]=[C:16]([O:20][C:21]4[CH:22]=[CH:23][N:24]=[CH:25][CH:26]=4)[CH:15]=3)[C:3]=2[C:4](=[O:10])[CH2:5]1

Participants

3

Reactant 2

HCID 1366803-Amino-5,5-dimethyl-2-cyclohexen-1-oneHCID 221178733-(4-Pyridyloxy)-benzaldehyde dimethyl acetal

Product 1

HCID 221178613,4,6,7,9,10-hexahydro-3,3,6,6-tetramethyl-9-[3-(4-pyridyloxy)-phenyl]-1,8(2H,5H)-acridinedione

Procedure

3-Amino-5,5-dimethyl-2-cyclohexen-1-one was reacted with 3-(4-pyridyloxy)-benzaldehyde dimethyl acetal in an analogous manner to that described in Example 1 to give 3,4,6,7,9,10-hexahydro-3,3,6,6-tetramethyl-9-[3-(4-pyridyloxy)-phenyl]-1,8(2H,5H)-acridinedione. Purification by column chromatography on silica gel using dichloromethane/methanol (95:5) as the eluent gave a beige solid of melting point 186-188° C.

Sources & evidence

ORD record
ord-f8404beca6484ab482956a76923d2059
Source dataset
uspto-grants-1999_10
Patent number
US05969139

Reaction notes

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