Water → HCID 22117851, compound

HRID 1740462Notes

Reaction equation

HRID 1740462 reaction equation
[NH2:1][C:2]1[CH2:7][C:6]([CH3:9])([CH3:8])[CH2:5][C:4](=[O:10])[CH:3]=1.[CH3:11][CH:12]1[CH2:17][C:16](=[O:18])[CH2:15][C:14](=O)[CH2:13]1.[Br:20][C:21]1[CH:28]=[CH:27][C:24]([CH:25]=O)=[CH:23][CH:22]=1.O>C(O)C.C(O)(=O)C>[Br:20][C:21]1[CH:28]=[CH:27][C:24]([CH:25]2[C:3]3[C:4](=[O:10])[CH2:5][C:6]([CH3:9])([CH3:8])[CH2:7][C:2]=3[NH:1][C:14]3[CH2:13][CH:12]([CH3:11])[CH2:17][C:16](=[O:18])[C:15]2=3)=[CH:23][CH:22]=1

Participants

7

Reactant 4

HCID 962WaterHCID 707414-BromobenzaldehydeHCID 1366803-Amino-5,5-dimethyl-2-cyclohexen-1-oneHCID 4580955-Methylcyclohexane-1,3-dione

Product 1

HCID 22117851HCID 22117851, compound

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 702EthanolSolvent

Procedure

A solution of 1.39 g of 3-amino-5,5-dimethyl-2-cyclohexen-1-one, 1.26 g of 5-methyl-cyclohexane-1,3-dione and 1.51 g of 4-bromobenzaldehyde in 18 ml of absolute ethanol and 6 ml of glacial acetic acid was heated under reflux under a nitrogen atmosphere for 12 hours. The mixture was then cooled to room temperature and about 10 ml of water was added until the product precipitated. The product was filtered off and washed with three 50 ml portions of cold diethyl ether to give 9-(4-bromophenyl)-3,4,6,7,9,10-hexahydro-3,3,6(RS)-trimethyl-1,8(2H,5H)-acridinedione as a pale yellow solid. The product was shown to be a 9:1 mixture of diastereoisomers by HPLC and gave a mass ion of 414 (FAB, [M+H]+).

Workup

  1. temperatureunder reflux under a nitrogen atmosphere for 12 hours
  2. customprecipitated
  3. filtrationThe product was filtered off
  4. washwashed with three 50 ml portions of cold diethyl ether

Sources & evidence

ORD record
ord-a5999bc42d0f4691b78d0dba153c3a2f
Source dataset
uspto-grants-1999_10
Patent number
US05969139

Reaction notes

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