3-Amino-5,5-dimethyl-2-cyclohexen-1-one → 4-(2,3,4,5,6,7,8,9-octahydro-3,3,6,6-tetramethyl-1,8-dioxo-1H-acridin-9-yl)-2-nitrobenzonitrile

HRID 1740428Notes

Reaction equation

HRID 1740428 reaction equation
[NH2:1][C:2]1[CH2:7][C:6]([CH3:9])([CH3:8])[CH2:5][C:4](=[O:10])[CH:3]=1.[C:11]([C:13]1[CH:20]=[CH:19][C:16]([CH:17]=O)=[CH:15][C:14]=1[N+:21]([O-:23])=[O:22])#[N:12]>>[CH3:8][C:6]1([CH3:9])[CH2:7][C:2]2[N:1]=[C:2]3[CH:3]([C:4](=[O:10])[CH2:5][C:6]([CH3:9])([CH3:8])[CH2:7]3)[CH:17]([C:16]3[CH:19]=[CH:20][C:13]([C:11]#[N:12])=[C:14]([N+:21]([O-:23])=[O:22])[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 221178154-Formyl-2-nitrobenzonitrile

Product 1

HCID 221178714-(2,3,4,5,6,7,8,9-octahydro-3,3,6,6-tetramethyl-1,8-dioxo-1H-acridin-9-yl)-2-nitrobenzonitrile

Procedure

Reaction of 3-amino-5,5-dimethyl-2-cyclohexen-1-one with 4-cyano-3-nitrobenzaldehyde in an analogous manner to that described in Example 1 gave 4-(2,3,4,5,6,7,8,9-octahydro-3,3,6,6-tetramethyl-1,8-dioxo-1H-acridin-9-yl)-2-nitrobenzonitrile. Crystallization from methanol gave a yellow crystalline solid of melting point 274-275° C.

Sources & evidence

ORD record
ord-55e74250b82d457f92f630ef469fa739
Source dataset
uspto-grants-1999_10
Patent number
US05969139

Reaction notes

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