Potassium Hydroxide → 2-Ethyl-6-methoxy-1-methyl-1H-indole-3-carboxylic acid

HRID 985278Notes

Reaction equation

HRID 985278 reaction equation
[OH-:1].[K+].[CH2:3]([C:5]1[N:6]([CH3:22])[C:7]2[C:12]([C:13]=1[C:14](=[O:19])C(F)(F)F)=[CH:11][CH:10]=[C:9]([O:20][CH3:21])[CH:8]=2)[CH3:4]>O.CCO>[CH2:3]([C:5]1[N:6]([CH3:22])[C:7]2[C:12]([C:13]=1[C:14]([OH:19])=[O:1])=[CH:11][CH:10]=[C:9]([O:20][CH3:21])[CH:8]=2)[CH3:4]

Participants

5

Reactant 2

HCID 14797Potassium HydroxideHCID 221436071-(2-Ethyl-6-methoxy-1-methyl-1H-indol-3-yl)-2,2,2-trifluoro-ethanone

Product 1

HCID 221435852-Ethyl-6-methoxy-1-methyl-1H-indole-3-carboxylic acidYield 72%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

KOH (1.9 g, 33.49 mmole) in 20 ml H2O was added to a solution of 1-(2-ethyl-6-methoxy-1-methyl-1H-indol-3-yl)-2,2,2-trifluoro-ethanone 73d (2.42 g, 8.47 mmole) in 20 ml EtOH. The reaction mixture was heated to reflux for 8 h and concentrated. The residue was dissolved in H2O acidified with 1N HCl to pH ˜1 and filtrated. The solid was purified by flash column chromatography (2-5% CH3OH in CH2Cl2) to give yellow color solid (1.3 g, 72%). 1H NMR (CDCl3) δ11.88 (1H, bs), 7.82 (1H, d, J=8.7 Hz), 7.04 (1H, s), 6.77 (1H, d, J=8.7 Hz), 3.80 (3H, s), 3.70 (3H, s), 3.51 (2H, q, J=7.4 Hz), 1.15 (3H, t, J=7.4 Hz). ESIMS (MH+): 234.05.

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureto reflux for 8 h
  3. concentrationconcentrated
  4. dissolutionThe residue was dissolved in H2O
  5. filtrationfiltrated
  6. customThe solid was purified by flash column chromatography (2-5% CH3OH in CH2Cl2)

Sources & evidence

ORD record
ord-ed0a8e62048d48979d1e47d62912d728
Source dataset
uspto-grants-2005_03
Patent number
US06869962B2

Reaction notes

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