Sodium Hydroxide → 6-chloro-7-fluoro-1H-indole-2-carboxylic acid

HRID 844204Notes

Reaction equation

HRID 844204 reaction equation
[Cl:1][C:2]1[C:10]([F:11])=[C:9]2[C:5]([CH:6]=[C:7]([C:12]([O:14]C)=[O:13])[NH:8]2)=[CH:4][CH:3]=1.[OH-].[Na+]>O1CCCC1>[Cl:1][C:2]1[C:10]([F:11])=[C:9]2[C:5]([CH:6]=[C:7]([C:12]([OH:14])=[O:13])[NH:8]2)=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 22612708methyl 6-chloro-7-fluoro-1H-indole-2-carboxylate

Product 1

HCID 223380796-chloro-7-fluoro-1H-indole-2-carboxylic acidYield 98.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A stirred solution of methyl 6-chloro-7-fluoroindole-2-carboxylate (2.3 g, 10 mmol), tetrahydrofuran (20 mL) and aqueous sodium hydroxide solution (2 N, 20 mL) was heated under reflux for 16 h. The mixture was cooled to room temperature and partitioned between aqueous sulfiuric acid (2 M, 30 mL) and ethyl acetate (3×30 mL). The combined organic extracts were dried (magnesium sulfate) and concentrated in vacuo to give the product (2.1 g, 98% yield) as a white solid: IR νmax (Nujol)/cm−1 1681, 1557, 1263, 1206, 926 and 840; NMR δH (400 MHz, DMSO-d6) 7.01-7.12 (2H, m) and 7.31-7.34 (1H, m).

Workup

  1. temperatureunder reflux for 16 h
  2. custompartitioned between aqueous sulfiuric acid (2 M, 30 mL) and ethyl acetate (3×30 mL)
  3. dry with materialThe combined organic extracts were dried (magnesium sulfate)
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-7578407c681a400aac7baab1d55c35a5
Source dataset
uspto-grants-2002_04
Patent number
US06380238B1

Reaction notes

Loading…