Sodium Hydroxide → 5,6-Difluoro-1H-indole-2-carboxylic acid

HRID 2396841Notes

Reaction equation

HRID 2396841 reaction equation
[F:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][C:10]=1[F:11])[NH:7][C:6]([C:12]([O:14]CC)=[O:13])=[CH:5]2.[OH-].[Na+]>C(O)C>[F:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][C:10]=1[F:11])[NH:7][C:6]([C:12]([OH:14])=[O:13])=[CH:5]2

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 18986234Ethyl 5,6-difluoro-1H-indole-2-carboxylate

Product 1

HCID 189862515,6-Difluoro-1H-indole-2-carboxylic acidYield 98.8%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 2.06 g of ethyl 5,6-difluoroindole-2-carboxylate in 90 ml of ethanol was treated with 45 ml of 2N sodium hydroxide solution and stirred at room temperature for 17 hours. The alcohol was evaporated and the residue was treated with 50 ml of 2N hydrochloric acid. The separated crystals were filtered off, washed with water and dried. 1.78 g (98.8%) of 5,6-difluoroindole-2-carboxylic acid were obtained as brown crystals with m.p. 279°-280°.

Workup

  1. customThe alcohol was evaporated
  2. additionthe residue was treated with 50 ml of 2N hydrochloric acid
  3. filtrationThe separated crystals were filtered off
  4. washwashed with water
  5. customdried

Sources & evidence

ORD record
ord-a3cb0abf257643de81ed4434135e65e8
Source dataset
uspto-grants-1996_02
Patent number
US05494928

Reaction notes

Loading…