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

HRID 1740433Notes

Reaction equation

HRID 1740433 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]([N:20]2[CH:24]=[CH:23][N:22]=[CH:21]2)[CH:15]=1>>[N:20]1([C:16]2[CH:15]=[C:14]([CH:13]3[C:3]4[C:4](=[O:10])[CH2:5][C:6]([CH3:9])([CH3:8])[CH2:7][C:2]=4[NH:1][C:2]4[CH2:7][C:6]([CH3:9])([CH3:8])[CH2:5][C:4](=[O:10])[C:3]3=4)[CH:19]=[CH:18][CH:17]=2)[CH:24]=[CH:23][N:22]=[CH:21]1

Participants

3

Reactant 2

HCID 1366803-Amino-5,5-dimethyl-2-cyclohexen-1-oneHCID 221178243-(1-Imidazolyl)-benzaldehyde dimethyl acetal

Product 1

HCID 221178323,4,6,7,9,10-hexahydro-9-[3-(1-imidazolyl)-phenyl]-3,3,6,6-tetramethyl-1,8(2H,5H)-acridinedione

Procedure

Reaction of 3-amino-5,5-dimethyl-2-cyclohexen-1-one with 3-(1-imidazolyl)-benzaldehyde dimethyl acetal in an analogous manner to that described in Example 1 gave 3,4,6,7,9,10-hexahydro-9-[3-(1-imidazolyl)-phenyl]-3,3,6,6-tetramethyl-1,8(2H,5H)-acridinedione. Crystallization from methanol/water gave a yellow crystalline solid of melting point 286-288° C.

Sources & evidence

ORD record
ord-9ab5d731ffa04464b6ff35e0750e7dbd
Source dataset
uspto-grants-1999_10
Patent number
US05969139

Reaction notes

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