Hydrochloric Acid → HCID 59529914, compound

HRID 1894943Notes

Reaction equation

HRID 1894943 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([F:16])[CH:5]=[C:6]2[C:10]=1[NH:9][C:8]([C:11]([O:13]CC)=[O:12])=[CH:7]2.[OH-].[Na+].Cl>CO>[Cl:1][C:2]1[CH:3]=[C:4]([F:16])[CH:5]=[C:6]2[C:10]=1[NH:9][C:8]([C:11]([OH:13])=[O:12])=[CH:7]2

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 404243151H-Indole-2-carboxylic acid, 7-chloro-5-fluoro-, ethyl ester

Product 1

HCID 59529914HCID 59529914, compoundYield 95%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 250 mg of ethyl 7-chloro-5-fluoro-1H-indole-2-carboxylate in 2 mL of methanol was added 5 mL of 1M aqueous sodium hydroxide solution, followed by stirring at room temperature for 3 hours. The reaction liquid was adjusted to an acidic condition by adding a 1M aqueous hydrochloric acid solution, followed by extraction with ethyl acetate. The organic layer was washed with saturated brine, dried over anhydrous sodium sulfate and then concentrated under reduced pressure to obtain 210 mg of 7-chloro-5-fluoro-1H-indole-2-carboxylic acid as a white solid.

Workup

  1. customThe reaction liquid
  2. extractionfollowed by extraction with ethyl acetate
  3. washThe organic layer was washed with saturated brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-d3c55696f20a45aeb9d0d292078e0f83
Source dataset
uspto-grants-2013_08
Patent number
US08513422B2

Reaction notes

Loading…