Ethanol → HCID 58763425, compound

HRID 858287Notes

Reaction equation

HRID 858287 reaction equation
[C:1]([CH2:4][C:5]1[C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[N:7]([C:14]2[CH:19]=[CH:18][CH:17]=[C:16]([C:20]([OH:22])=[O:21])[CH:15]=2)[C:6]=1[C:23]([OH:25])=[O:24])([OH:3])=[O:2].OS(O)(=O)=O.[CH2:31](O)[CH3:32]>O>[C:20]([C:16]1[CH:15]=[C:14]([N:7]2[C:8]3[C:13](=[CH:12][CH:11]=[CH:10][CH:9]=3)[C:5]([CH2:4][C:1]([O:3][CH2:31][CH3:32])=[O:2])=[C:6]2[C:23]([OH:25])=[O:24])[CH:19]=[CH:18][CH:17]=1)([OH:22])=[O:21]

Participants

5

Reactant 3

HCID 702EthanolHCID 1118Sulfuric AcidHCID 58763423HCID 58763423, compound

Product 1

HCID 58763425HCID 58763425, compoundYield 94%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a solution of solution of 3-carboxymethyl-1-(3-carboxy-phenyl)-1H-indole-2-carboxylic acid (0.743 g, 2.2 mmol) in ethanol (5 mL) was added a drop of conc. H2SO4 and the mixture was stirred at room temperature for 2.5 h. The reaction mixture was diluted with water (50 mL) and extracted with EtOAc (50 mL). The extract was washed with brine, dried over MgSO4 and concentrated to give 0.94 g of 1-(3-carboxy-phenyl)-3-ethoxycarbonylmethyl-1H-indole-2-carboxylic acid as a yellow oil (94% yield): 1H NMR (CDCl3, 300 MHz) δ 1.17 (t, J=7.25 Hz, 3H), 4.09 (q, J=7.05 Hz, 2H), 4.18 (s, 2H), 7.04 (d, J=8.39 Hz, 1H), 7.20 (t, J=7.25 Hz, 1H), 7.30 (t, J=7.25 Hz, 1H), 7.71–7.60 (m, 2H), 7.76–7.80 (m, 2H), 8.02 (d, J=7.06 Hz, 1H).

Workup

  1. extractionextracted with EtOAc (50 mL)
  2. washThe extract was washed with brine
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-977adc9de60c42129b44eda2b22c1b62
Source dataset
uspto-grants-2006_12
Patent number
US07148250B2

Reaction notes

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