Diethyl Succinate → HCID 21577756, compound

HRID 1278082Notes

Reaction equation

HRID 1278082 reaction equation
[Cl:1][C:2]1[CH:10]=[CH:9][C:5]([CH2:6][C:7]#[N:8])=[CH:4][CH:3]=1.C([O:13][C:14](=O)[CH2:15][CH2:16]C(OCC)=O)C.C([O-])C.[Na+]>>[Cl:1][C:2]1[CH:10]=[CH:9][C:5]([CH2:6][CH:7]2[NH:8][C:14](=[O:13])[CH2:15][CH2:16]2)=[CH:4][CH:3]=1

Participants

4

Reactant 3

HCID 31249Diethyl SuccinateHCID 2415824-Chlorobenzyl cyanideHCID 2723922Sodium ethoxide

Product 1

HCID 21577756HCID 21577756, compound

Procedure

Condense 4-chlorobenzylcyanide with succinic acid diethyl ester in the presence of sodium ethanolate, boil the condensation product (without further purification) with a mixture of glacial acetic acid/semi-concentrated hydrochloric acid for 20 hours under reflux, convert (with hydroxylamine) the thus-obtained 5-(4-chlorophenyl)-4-oxo-pentanoic acid (m.p. 91° to 93°) into 5-(4-chlorophenyl)-4-hydroxyiminopentanoic acid (m.p. 116° to 117°), hydrogenate the latter with platinum/activated charcoal/hydrogen in acetic acid to 5-(4-chlorophenyl)-4-aminopentanoic acid and cyclize the thus-substituted pentanoic acid (through boiling in dioxane) to obtain 5-(4-chlorobenzyl)pyrrolidin-2-one (m.p. 95° to 98°).

Workup

  1. customthe condensation product (without further purification)
  2. additionwith a mixture of glacial acetic acid/semi-concentrated hydrochloric acid for 20 hours
  3. temperatureunder reflux

Sources & evidence

ORD record
ord-138c7094d69d4870b914feb2bfda6f46
Source dataset
uspto-grants-1981_07
Patent number
US04279918

Reaction notes

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