Water → 3-Hydroxy-5-(2-oxopyrrolidin-1-yl)benzoic acid

HRID 1612432Notes

Reaction equation

HRID 1612432 reaction equation
N[C:2]1[CH:3]=[C:4]([CH:8]=[C:9]([N:11]2[CH2:15][CH2:14][CH2:13][C:12]2=[O:16])[CH:10]=1)[C:5]([OH:7])=[O:6].N([O-])=[O:18].[Na+].O>Cl.CO>[OH:18][C:2]1[CH:3]=[C:4]([CH:8]=[C:9]([N:11]2[CH2:15][CH2:14][CH2:13][C:12]2=[O:16])[CH:10]=1)[C:5]([OH:7])=[O:6]

Participants

6

Reactant 3

HCID 962WaterHCID 222529903-Amino-5-(2-oxo-pyrrolidin-1-yl)-benzoic acidHCID 23668193Sodium Nitrite

Product 1

HCID 222530273-Hydroxy-5-(2-oxopyrrolidin-1-yl)benzoic acid

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 887MethanolSolvent

Conditions

Temperature
90 °C

Procedure

This amine (1.10 g, 5.0 mmol) in 2N HCl (10 ml) and methanol (approx 15 ml, to aid solubility) was cooled in an ice bath and treated portionwise with sodium nitrite (0.76 g, 11.0 mmol) at such a rate to keep the temperature below 5° C. After completion of the addition, water (20 ml) was added and the mixture was heated at approx 90° C. for 1 hr. After cooling the product was extracted into ethyl acetate and the combined extracts were washed with brine and then dried over sodium sulfate and evaporated to give the title compound, 0.93 g.

Workup

  1. customthe temperature below 5° C
  2. additionwas added
  3. temperatureAfter cooling the product
  4. extractionwas extracted into ethyl acetate
  5. washthe combined extracts were washed with brine
  6. dry with materialdried over sodium sulfate
  7. customevaporated

Sources & evidence

ORD record
ord-e65e26ee8f8f4e81b89cce26b3876882
Source dataset
uspto-grants-2006_01
Patent number
US06992103B2

Reaction notes

Loading…