Tetrahydrofuran → 6-chloro-7-[methyl(2-thienylsulfonyl)amino]-1H-indole-2-carboxylic acid

HRID 1851616Notes

Reaction equation

HRID 1851616 reaction equation
[Cl:1][C:2]1[C:10]([N:11]([CH3:20])[S:12]([C:15]2[S:16][CH:17]=[CH:18][CH:19]=2)(=[O:14])=[O:13])=[C:9]2[C:5]([CH:6]=[C:7]([C:21]([O:23]CC)=[O:22])[NH:8]2)=[CH:4][CH:3]=1.[OH-].[Na+].O1CCCC1>CO>[Cl:1][C:2]1[C:10]([N:11]([CH3:20])[S:12]([C:15]2[S:16][CH:17]=[CH:18][CH:19]=2)(=[O:14])=[O:13])=[C:9]2[C:5]([CH:6]=[C:7]([C:21]([OH:23])=[O:22])[NH:8]2)=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 14798Sodium HydroxideHCID 57476030ethyl 6-chloro-7-[methyl(2-thienylsulfonyl)amino]-1H-indole-2-carboxylate

Product 1

HCID 574760316-chloro-7-[methyl(2-thienylsulfonyl)amino]-1H-indole-2-carboxylic acidYield 100.3%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
60 °C

Procedure

A mixture of ethyl 6-chloro-7-[methyl(2-thienylsulfonyl)amino]-1H-indole-2-carboxylate (0.74 g), 4N aqueous sodium hydroxide solution (1.2 mL), tetrahydrofuran (6 mL) and methanol (4 mL) was stirred at 60° C. for 2 hr. The reaction mixture was concentrated and acidified with 10% aqueous citric acid solution. The resulting crystals were filtrated, washed with water, and dried to give the title compound (0.69 g, quantitative) as colorless crystals. melting point 286-288° C.

Workup

  1. concentrationThe reaction mixture was concentrated
  2. filtrationThe resulting crystals were filtrated
  3. washwashed with water
  4. customdried

Sources & evidence

ORD record
ord-c10be613acb84aceb0ba38df1db74f68
Source dataset
uspto-grants-2015_02
Patent number
US08957070B2

Reaction notes

Loading…