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

HRID 2416569Notes

Reaction equation

HRID 2416569 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 monomethyl terephthalate chloride was reacted with 14.2 g (200 mmol) of pyrrolidine and 21.0 g (208 mmol) of triethylamine in 350 ml of dichloromethane. After the treatment in an ordinary manner, methyl 4-(1-pyrrolidylcarbonyl)benzoate was obtained. 29.0 g of the ester 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 evaporated. 1 N hydrochloric acid was added to the residue and the obtained mixture was treated with dichloromethane as the extraction solvent in an ordinary manner to obtain the title compound.

Workup

  1. customAfter the completion of the reaction
  2. customthe solvent was evaporated
  3. addition1 N hydrochloric acid was added to the residue
  4. additionthe obtained mixture was treated with dichloromethane as the extraction solvent in an ordinary manner

Sources & evidence

ORD record
ord-0ef5564662d44654a1df328c6dc721f6
Source dataset
uspto-grants-2004_11
Patent number
US06825181B1

Reaction notes

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