3-Amino-5-(2-oxo-pyrrolidin-1-yl)-benzoic acid → 3-Hydroxy-5-(2-oxopyrrolidin-1-yl)benzoic acid

HRID 1664225Notes

Reaction equation

HRID 1664225 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>[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

4

Reactant 2

HCID 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 1

HCID 962WaterSolvent2×

Conditions

Temperature
90 °C

Procedure

To the solution of 1.33 g (6.0 mmol) 3-amino-5-(2-oxo-pyrrolidin-1-yl)-benzoic acid in 15 ml water and 0.75 ml (13.3 mmol, 2.2 eq) concentrated sulfuric at 0° C. are added 0.56 g (8.2 mmol, 1.35 eq) sodium nitrit. After addition of 10 ml water the reaction is heated to 90° C. After cooling to rt the reaction is extracted with EtOAc, the organic layer is dried over sodium sulfate and the solvent is evaporated at reduced pressure to give the product.

Workup

  1. temperatureAfter cooling to rt the reaction
  2. extractionis extracted with EtOAc
  3. dry with materialthe organic layer is dried over sodium sulfate
  4. customthe solvent is evaporated at reduced pressure
  5. customto give the product

Sources & evidence

ORD record
ord-2ed502b0e1c54cad8b28c1ce94ae6127
Source dataset
uspto-grants-2011_10
Patent number
US08039455B2

Reaction notes

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