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

HRID 1851499Notes

Reaction equation

HRID 1851499 reaction equation
[CH3:1][N:2]([S:17]([C:20]1[S:21][CH:22]=[CH:23][CH:24]=1)(=[O:19])=[O:18])[C:3]1[CH:4]=[CH:5][CH:6]=[C:7]2[C:11]=1[NH:10][C:9]([C:12]([O:14]CC)=[O:13])=[CH:8]2.[OH-].[Na+].O1CCCC1>CO>[CH3:1][N:2]([S:17]([C:20]1[S:21][CH:22]=[CH:23][CH:24]=1)(=[O:19])=[O:18])[C:3]1[CH:4]=[CH:5][CH:6]=[C:7]2[C:11]=1[NH:10][C:9]([C:12]([OH:14])=[O:13])=[CH:8]2

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 14798Sodium HydroxideHCID 57475952ethyl 7-[methyl(2-thienylsulfonyl)amino]-1H-indole-2-carboxylate

Product 1

HCID 574759517-[methyl(2-thienylsulfonyl)amino]-1H-indole-2-carboxylic acidYield 94.8%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
60 °C

Procedure

A mixture of ethyl 7-[methyl(2-thienylsulfonyl)amino]-1H-indole-2-carboxylate (0.40 g), 8N aqueous sodium hydroxide solution (0.40 mL), tetrahydrofuran (5 mL) and methanol (5 mL) was stirred at 60° C. for 1 hr. The reaction mixture was concentrated, and water was added to the residue. The mixture was acidified with 10% aqueous citric acid solution, and the resulting crystals were filtrated, washed with water, and dried to give the title compound (0.35 g, yield 91%) as colorless crystals. melting point>240° C. (decomposition).

Workup

  1. concentrationThe reaction mixture was concentrated
  2. additionwater was added to the residue
  3. filtrationthe resulting crystals were filtrated
  4. washwashed with water
  5. customdried

Sources & evidence

ORD record
ord-5e6dc04ffb2b442b8463ae9fec096a91
Source dataset
uspto-grants-2015_02
Patent number
US08957070B2

Reaction notes

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