Citric Acid → HCID 86619905, compound

HRID 1960342Notes

Reaction equation

HRID 1960342 reaction equation
[Cl:1][C:2]1[C:7]([S:8]([N:11]([CH3:27])[C:12]2[CH:13]=[CH:14][C:15]([CH3:26])=[C:16]3[C:20]=2[NH:19][C:18]([C:21]([O:23]CC)=[O:22])=[CH:17]3)(=[O:10])=[O:9])=[CH:6][CH:5]=[CH:4][N:3]=1.[OH-].[Na+].CO.C(O)(=O)CC(CC(O)=O)(C(O)=O)O>O1CCCC1>[Cl:1][C:2]1[C:7]([S:8]([N:11]([CH3:27])[C:12]2[CH:13]=[CH:14][C:15]([CH3:26])=[C:16]3[C:20]=2[NH:19][C:18]([C:21]([OH:23])=[O:22])=[CH:17]3)(=[O:10])=[O:9])=[CH:6][CH:5]=[CH:4][N:3]=1

Participants

6

Reactant 4

HCID 311Citric AcidHCID 887MethanolHCID 14798Sodium HydroxideHCID 59135710HCID 59135710, compound

Product 1

HCID 86619905HCID 86619905, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
50 °C

Procedure

A mixture of ethyl 7-[[(2-chloropyridin-3-yl)sulfonyl](methyl)amino]-4-methyl-1H-indole-2-carboxylate (0.86 g), 1N aqueous sodium hydroxide solution (4.2 mL), methanol (6 mL) and tetrahydrofuran (6 mL) was stirred at 50° C. for 1 hr. 10% Aqueous citric acid solution was added to the reaction mixture, and the mixture was concentrated. The resulting crystals were collected by filtration, washed with water, dried, and concentrated to give 7-[[(2-chloropyridin-3-yl)sulfonyl](methyl)amino]-4-methyl-1H-indole-2-carboxylic acid as crude crystals.

Workup

  1. concentrationthe mixture was concentrated
  2. filtrationThe resulting crystals were collected by filtration
  3. washwashed with water
  4. customdried
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-7573b670f6a047daac8b57b4a1997742
Source dataset
uspto-grants-2013_04
Patent number
US08410087B2

Reaction notes

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