Citric Acid → HCID 57901602, compound

HRID 1851490Notes

Reaction equation

HRID 1851490 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:9](=[C:10]([NH:12][S:13]([C:16]3[S:17][CH:18]=[CH:19][CH:20]=3)(=[O:15])=[O:14])[CH:11]=1)[NH:8][C:7]([C:21]([O:23]CC)=[O:22])=[CH:6]2.CO.[OH-].[K+].C(O)(=O)CC(CC(O)=O)(C(O)=O)O>O1CCCC1>[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:9](=[C:10]([NH:12][S:13]([C:16]3[S:17][CH:18]=[CH:19][CH:20]=3)(=[O:15])=[O:14])[CH:11]=1)[NH:8][C:7]([C:21]([OH:23])=[O:22])=[CH:6]2

Participants

6

Reactant 4

HCID 311Citric AcidHCID 887MethanolHCID 14797Potassium HydroxideHCID 57901653HCID 57901653, compound

Product 1

HCID 57901602HCID 57901602, compoundYield 96%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a mixed solution of ethyl 5-methoxy-7-[(2-thienylsulfonyl)amino]-1H-indole-2-carboxylate (0.34 g) in tetrahydrofuran (10 mL)-methanol (10 mL) was added aqueous solution (5 mL) of 85% potassium hydroxide (0.20 g), and the mixture was stirred at room temperature for 15 hr. Aqueous citric acid solution was added to the reaction mixture, and the mixture was extracted with ethyl acetate, washed with saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The obtained crystals were washed with ethyl acetate-hexane to give the title compound (300 mg, yield 96%) as pale-yellow crystals. melting point>240° C. (decomposition).

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washwashed with saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. washThe obtained crystals were washed with ethyl acetate-hexane

Sources & evidence

ORD record
ord-029eeebeb4e3404cb3a5025de3d214d9
Source dataset
uspto-grants-2015_02
Patent number
US08957070B2

Reaction notes

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