Indole-3-Carboxylic Acid → HCID 4127568, compound

HRID 1393673Notes

Reaction equation

HRID 1393673 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3]([C:10]([OH:12])=[O:11])=[CH:2]1.[C:13]([O-])(=[O:15])[CH3:14].[Na+]>C(OC(=O)C)(=O)C>[C:13]([N:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3]([C:10]([OH:12])=[O:11])=[CH:2]1)(=[O:15])[CH3:14]

Participants

4

Reactant 2

HCID 69867Indole-3-Carboxylic AcidHCID 517045Sodium Acetate

Product 1

HCID 4127568HCID 4127568, compoundYield 34%

Reagents, catalysts & solvents 1

HCID 7918Acetic AnhydrideSolvent

Conditions

Temperature
110 °C

Procedure

1H-Indole-3-carboxylic acid (400 mg) and sodium acetate (0.96 g) were suspended in acetic anhydride (4.8 ml). The mixture was stirred at 110° C. for 16 hours and extracted with chloroform. The organic phase was washed with 2 N hydrochloric acid, dried over sodium sulfate anhydrous, and concentrated under reduced pressure. The residue was purified by column chromatography (eluting solvent; dichloromethane:methanol 50:1) to give the title compound (170 mg, Y.:34%).

Workup

  1. extractionextracted with chloroform
  2. washThe organic phase was washed with 2 N hydrochloric acid
  3. dry with materialdried over sodium sulfate anhydrous
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by column chromatography (eluting solvent; dichloromethane:methanol 50:1)

Sources & evidence

ORD record
ord-c2936e8e5eca4e6b8a195e5c84b99f8e
Source dataset
uspto-grants-2008_03
Patent number
US07345180B2

Reaction notes

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