Methanol → HCID 20761749, compound

HRID 983003Notes

Reaction equation

HRID 983003 reaction equation
[NH:1]1[C:9]2[C:4](=[C:5]([C:10]3[CH:11]=[C:12]([CH2:16][C:17]([OH:19])=[O:18])[CH:13]=[CH:14][CH:15]=3)[CH:6]=[CH:7][CH:8]=2)[CH:3]=[CH:2]1.[CH3:20]O>Cl.O1CCOCC1>[CH3:20][O:18][C:17](=[O:19])[CH2:16][C:12]1[CH:13]=[CH:14][CH:15]=[C:10]([C:5]2[CH:6]=[CH:7][CH:8]=[C:9]3[C:4]=2[CH:3]=[CH:2][NH:1]3)[CH:11]=1

Participants

5

Reactant 2

HCID 887MethanolHCID 22561865HCID 22561865, compound

Product 1

HCID 20761749HCID 20761749, compoundYield 88%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidCatalystHCID 312751,4-DioxaneSolvent

Procedure

A mixture of [3-(1H-indol-4-yl)-phenyl]-acetic acid (4 g, 15.9 mmol), 4N HCl (20 drops) in methanol (30 mL) and dioxane was stirred at rt for 4 hours. The reaction was concentrated, diluted in ethyl acetate, washed with NaHCO3 (2×), brine (2×), dried and concentrated to give 3.72 g (88%) of [3-(1H-Indol-4-yl)phenyl]-acetic acid methyl ester. General Procedure for the Syntheses of the Precursor, 4-Aryl-1,3-dihydro-indol 2-one

Workup

  1. concentrationThe reaction was concentrated
  2. additiondiluted in ethyl acetate
  3. washwashed with NaHCO3 (2×), brine (2×)
  4. customdried
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-f20d2b4726bc4b56a9f05856ffd7f548
Source dataset
uspto-grants-2005_03
Patent number
US06861418B2

Reaction notes

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