Water → 3-(3'-Oxobutyl)benzamide

HRID 638641Notes

Reaction equation

HRID 638641 reaction equation
[C:1]([C:3]1[CH:4]=[C:5]([CH2:9][CH:10]([C:16](=[O:18])[CH3:17])C(OCC)=O)[CH:6]=[CH:7][CH:8]=1)#[N:2].[OH2:19]>Cl>[O:18]=[C:16]([CH3:17])[CH2:10][CH2:9][C:5]1[CH:4]=[C:3]([CH:8]=[CH:7][CH:6]=1)[C:1]([NH2:2])=[O:19]

Participants

4

Reactant 2

HCID 962WaterHCID 20252807Ethyl 2-(3'-cyanophenylmethyl)-3-oxobutyrate

Product 1

HCID 135636403-(3'-Oxobutyl)benzamide

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

38.2 g of ethyl 2-(3'-cyanophenylmethyl)-3-oxobutyrate was heated for 2 hours under reflux in 500 ml of concentrated hydrochloric acid. To the reaction solution was added 500 ml of water, followed by extraction three times with 500 ml portions of ethyl acetate. The organic phase was washed with water and dried with anhydrous sodium sulfate, after which the solvent was distilled off. The resultant 3-(3'-oxobutyl)benzoic acid was admixed with 500 ml of benzene and 17 ml of thionyl chloride and heated for 2 hours under reflux. The reaction solution was dropped into ice-cooled concentrated ammonia water and the resultant amide extracted three times with 500 ml portions of ethyl acetate. The organic phase was washed with a saturated saline solution and dried with anhydrous sodium sulfate. The solvent was distilled off and the residue recrystallized from ethyl acetate-n-hexane to obtained 23.1 g of 3-(3'-oxobutyl)benzamide, melting point 122°-125° C.

Workup

  1. extractionfollowed by extraction three times with 500 ml portions of ethyl acetate
  2. washThe organic phase was washed with water
  3. dry with materialdried with anhydrous sodium sulfate
  4. distillationafter which the solvent was distilled off
  5. temperatureheated for 2 hours
  6. temperatureunder reflux
  7. additionThe reaction solution was dropped into ice-
  8. temperaturecooled concentrated ammonia water
  9. extractionthe resultant amide extracted three times with 500 ml portions of ethyl acetate
  10. washThe organic phase was washed with a saturated saline solution
  11. dry with materialdried with anhydrous sodium sulfate
  12. distillationThe solvent was distilled off
  13. customthe residue recrystallized from ethyl acetate-n-hexane

Sources & evidence

ORD record
ord-acde151f82a0454c93353e5b856b13ba
Source dataset
uspto-grants-1985_12
Patent number
US04562206

Reaction notes

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