2-Methylbenzenesulfonic acid → HCID 15007047, compound

HRID 1110355Notes

Reaction equation

HRID 1110355 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-217bf0065e7c4c6b91b5cfda5a6d5409
Source dataset
uspto-grants-1990_12
Patent number
US04975431

Reaction notes

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