Sodium Hydroxide → 1H-pyrrolo[2,3-b]pyridine-4-carboxylic acid

HRID 549078Notes

Reaction equation

HRID 549078 reaction equation
[NH:1]1[C:5]2[N:6]=[CH:7][CH:8]=[C:9]([C:10]([O:12]C)=[O:11])[C:4]=2[CH:3]=[CH:2]1.[OH-].[Na+]>CO>[NH:1]1[C:5]2[N:6]=[CH:7][CH:8]=[C:9]([C:10]([OH:12])=[O:11])[C:4]=2[CH:3]=[CH:2]1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 22832048Methyl 1H-pyrrolo[2,3-b]pyridine-4-carboxylate

Product 1

HCID 224774261H-pyrrolo[2,3-b]pyridine-4-carboxylic acidYield 66.4%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 1H-pyrrolo[2,3-b]pyridine-4 carboxylic acid, methyl ester [1.8 g, Reference Example 19(c)] in methanol (60 mL) was treated with sodium hydroxide solution (25 mL, 2N) and the mixture was stirred at room temperature for 2 hours then evaporated. The residue was treated with water (50 mL) and the pH of the mixture was adjusted to 34 by addition of hydrochloric acid. The resulting yellow solid was filtered, then washed well with water and then dried to give the title compound (1.1 g) as a yellow solid.

Workup

  1. customthen evaporated
  2. additionThe residue was treated with water (50 mL)
  3. additionthe pH of the mixture was adjusted to 34 by addition of hydrochloric acid
  4. filtrationThe resulting yellow solid was filtered
  5. washwashed well with water
  6. customdried

Sources & evidence

ORD record
ord-1e74e010998c4fe89144b08204b99297
Source dataset
uspto-grants-2011_05
Patent number
US07943616B2

Reaction notes

Loading…