Methanol → Benzoic acid, 4-(1-pyrrolidinylcarbonyl)-

HRID 747783Notes

Reaction equation

HRID 747783 reaction equation
[N:1]1([C:6]([C:8]2[CH:17]=[CH:16][C:11]([C:12]([O:14]C)=[O:13])=[CH:10][CH:9]=2)=[O:7])[CH2:5][CH2:4][CH2:3][CH2:2]1.[OH-].[Na+].O.CO>O1CCCC1>[N:1]1([C:6]([C:8]2[CH:17]=[CH:16][C:11]([C:12]([OH:14])=[O:13])=[CH:10][CH:9]=2)=[O:7])[CH2:2][CH2:3][CH2:4][CH2:5]1

Participants

6

Reactant 4

HCID 887MethanolHCID 962WaterHCID 14798Sodium HydroxideHCID 17178210Methyl 4-(pyrrolidine-1-carbonyl)benzoate

Product 1

HCID 10932939Benzoic acid, 4-(1-pyrrolidinylcarbonyl)-

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

29.0 g (0.146 mol) of 4-chlorocarbonyl benzoic acid monomethyl ester, 14.2 g (200 mmol) of pyrrolidine and 21.0 g (208 mmol) of triethylamine were reacted in 350 ml of dichloromethane. After the treatment in an ordinary manner, methyl 4-(1-pyrrolidylcarbonyl)benzoate was obtained. 29.0 g of this ester compound was hydrolyzed with 12.0 g of sodium hydroxide in a mixed solvent comprising 70 ml of water, 70 ml of methanol and 70 ml of tetrahydrofuran. After the completion of the reaction, the solvent was distilled off. After the addition of 1 N hydrochloric acid followed by the treatment with dichloromethane as the extractant in an ordinary manner, the title compound was obtained.

Workup

  1. customAfter the completion of the reaction
  2. distillationthe solvent was distilled off
  3. additionAfter the addition of 1 N hydrochloric acid

Sources & evidence

ORD record
ord-30e26ff36c744ea9839f604a2acd8947
Source dataset
uspto-grants-2008_07
Patent number
US07396844B1

Reaction notes

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