Sulfuric Acid → Cyclohexanone

HRID 1197817Notes

Reaction equation

HRID 1197817 reaction equation
[NH2:1][C:2]1[C:15]2[C:6](=[N:7][C:8]3[C:13]([CH:14]=2)=[CH:12][CH:11]=[CH:10][CH:9]=3)[C:5]([CH3:16])=[CH:4][CH:3]=1.[C:17]([CH2:20][C:21](=[O:23])[CH3:22])(=[O:19])[CH3:18].OS(O)(=O)=O>C(O)CCCC>[NH2:1][C:2]1[C:15]2[C:6](=[N:7][C:8]3[C:13]([CH:14]=2)=[CH:12][CH:11]=[CH:10][CH:9]=3)[C:5]([CH3:16])=[CH:4][CH:3]=1.[C:21]1(=[O:23])[CH2:22][CH2:2][CH2:18][CH2:17][CH2:20]1.[C:17]([CH2:20][C:21](=[O:23])[CH3:22])(=[O:19])[CH3:18]

Participants

7

Reactant 3

HCID 1118Sulfuric AcidHCID 31261AcetylacetoneHCID 11063652HCID 11063652, compound

Product 3

HCID 7967CyclohexanoneHCID 31261AcetylacetoneHCID 11063652HCID 11063652, compound

Reagents, catalysts & solvents 1

HCID 62761-PentanolSolvent

Procedure

Compound 11 was reduced with Na(Hg) to 1-amino-4-methylacridine 13 Heating compound 13 with acetylacetone and catalytic amounts of acid gave pure adduct 14, upon chromatography. Specifically, compound 14 was obtained by warming of compound 13 with acetylacetone in amylalcohol with traces of H2SO4 at 130° C. for 1.5hr. The structure of compound 14 C19H16N2O (eims, m/z 288, 100%) 1-acetyl-2,6-dimethylpyrido[2,3,4-k,l]acridine was elucidated mainly from its NMR data, by comparison of the chemical shifts with those of other pyridoacridines as described by He Hay-Yin et al., J.O.C., 56, 5369 (1991). Reacting compound 13 with cyclohexanone, instead of acetylacetone, gave compound 15. Specifically, compound 15 was obtained from cyclohexanone and compound 13 under the same conditions as compound 14.

Sources & evidence

ORD record
ord-86c23f5f980847069eabbd03d9e3356b
Source dataset
uspto-grants-1994_01
Patent number
US05278168

Reaction notes

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