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

HRID 1740423Notes

Reaction equation

HRID 1740423 reaction equation
[NH2:1][C:2]1[CH2:7][C:6]([CH3:9])([CH3:8])[CH2:5][C:4](=[O:10])[CH:3]=1.[F:11][C:12]1[CH:13]=[C:14]([CH:17]=[CH:18][C:19]=1[F:20])[CH:15]=O>>[F:11][C:12]1[CH:13]=[C:14]([CH:15]2[C:3]3[C:4](=[O:10])[CH2:5][C:6]([CH3:9])([CH3:8])[CH2:7][C:2]=3[NH:1][C:2]3[CH2:7][C:6]([CH3:9])([CH3:8])[CH2:5][C:4](=[O:10])[C:3]2=3)[CH:17]=[CH:18][C:19]=1[F:20]

Participants

3

Reactant 2

HCID 1366803-Amino-5,5-dimethyl-2-cyclohexen-1-oneHCID 5880883,4-Difluorobenzaldehyde

Product 1

HCID 221178469-(3,4-difluorophenyl)-3,4,6,7,9,10-hexahydro-3,3,6,6-tetramethyl-1,8(2H,5H)-acridinedione

Procedure

Reaction of 3-amino-5,5-dimethyl-2-cyclohexen-1-one with 3,4-difluorobenzaldehyde in an analogous manner to that described in Example 1 gave 9-(3,4-difluorophenyl)-3,4,6,7,9,10-hexahydro-3,3,6,6-tetramethyl-1,8(2H,5H)-acridinedione. Crystallization from absolute ethanol/water gave a pale yellow crystalline solid of melting point 270° C. (decomposition).

Sources & evidence

ORD record
ord-94a3a9649da445339f1b5c9bcc0f1d54
Source dataset
uspto-grants-1999_10
Patent number
US05969139

Reaction notes

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