2-Methylbenzenesulfonic acid → HCID 15007047, compound

HRID 1494543Notes

Reaction equation

HRID 1494543 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-1870cd19c4344b5185d0013778df8455
Source dataset
uspto-grants-1991_06
Patent number
US05026854

Reaction notes

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