2-Methylbenzenesulfonic acid → HCID 15007047, compound

HRID 1195724Notes

Reaction equation

HRID 1195724 reaction equation
[C:1]1(=[O:8])[CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.N1CCCC1.C1(C)C(S(O)(=O)=O)=CC=CC=1.[C:25](#[N:29])[C:26]([CH3:28])=[CH2:27]>C1(C)C=CC=CC=1.C(O)C.C(O)(=O)C>[C:25]([CH:26]([CH3:28])[CH2:27][CH:2]1[CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][C:1]1=[O:8])#[N:29]

Participants

8

Reactant 4

HCID 69252-Methylbenzenesulfonic acidHCID 10400CycloheptanoneHCID 31268PyrrolidineHCID 31368Methacrylonitrile

Product 1

HCID 15007047HCID 15007047, compound

Reagents, catalysts & solvents 3

HCID 176Acetic AcidSolventHCID 702EthanolSolventHCID 1140TolueneSolvent

Procedure

Cycloheptanone was converted to an enamine by reaction with pyrrolidine in toluene solvent and in the presence of toluenesulphonic acid. The enamine was alkylated with methacrylonitrile in ethanol solvent and hydrolysed using acetic acid according to the procedure of Stark et al, J. Amer. Chem, Soc., 85, 207 (1963) to give 2-(2-cyanopropyl)cycloheptanone (bp 100° C./0.02 mmHg).

Sources & evidence

ORD record
ord-6ced9daf49d94b76bfdb7a53a284b884
Source dataset
uspto-grants-1992_05
Patent number
US05112832

Reaction notes

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