Sodium Hydroxide → 3-Chloro-4-pyrrolidinobenzoic acid

HRID 2189772Notes

Reaction equation

HRID 2189772 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:10]=[CH:11][C:12]=1[N:13]1[CH2:17][CH2:16][CH2:15][CH2:14]1)[C:5]([O:7]CC)=[O:6].[OH-].[Na+]>C(O)C>[Cl:1][C:2]1[CH:3]=[C:4]([CH:10]=[CH:11][C:12]=1[N:13]1[CH2:17][CH2:16][CH2:15][CH2:14]1)[C:5]([OH:7])=[O:6]

Participants

4

Reactant 2

HCID 14798Sodium Hydroxide2×HCID 59316744Ethyl 3-chloro-4-(pyrrolidin-1-yl)benzoate

Product 1

HCID 47693833-Chloro-4-pyrrolidinobenzoic acidYield 59.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
40 °C

Procedure

A mixture of ethyl 3-chloro-4-(1-pyrrolidinyl)benzoate (D39) (685 mg, 2.71 mmol) and aqueous sodium hydroxide (2M, 1.36 mL, 2.72 mmol) in ethanol (15 mL) was heated at 40° C. for 17 h. Further sodium hydroxide (1.36 mL, 2.72 mmol) was added and the reaction heated for a further 8 h. The mixture was concentrated and the residue dissolved in water (100 mL). The aqueous phase was washed with ethyl acetate (2×100 mL) and then acidified to pH 6. A white solid formed and hence was filtered off, washed with water and dried in a vacuum oven to give the title compound as an off-white solid (362 mg). MS (ES): C11H1235ClNO2 requires 225; found 226 (MH+).

Workup

  1. temperaturethe reaction heated for a further 8 h
  2. concentrationThe mixture was concentrated
  3. dissolutionthe residue dissolved in water (100 mL)
  4. washThe aqueous phase was washed with ethyl acetate (2×100 mL)
  5. customA white solid formed
  6. filtrationhence was filtered off
  7. washwashed with water
  8. customdried in a vacuum oven

Sources & evidence

ORD record
ord-284a71f229a641c89fe1e3b137203614
Source dataset
uspto-grants-2012_12
Patent number
US08324254B2

Reaction notes

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