Sodium Hydroxide → 6-Methoxy-1-(propan-2-yl)-1H-indole-3-carboxylic acid

HRID 1816103Notes

Reaction equation

HRID 1816103 reaction equation
FC(F)(F)[C:3]([C:5]1[C:13]2[C:8](=[CH:9][C:10]([O:14][CH3:15])=[CH:11][CH:12]=2)[N:7]([CH:16]([CH3:18])[CH3:17])[CH:6]=1)=[O:4].[OH-:21].[Na+]>>[CH:16]([N:7]1[C:8]2[C:13](=[CH:12][CH:11]=[C:10]([O:14][CH3:15])[CH:9]=2)[C:5]([C:3]([OH:4])=[O:21])=[CH:6]1)([CH3:18])[CH3:17]

Participants

3

Reactant 2

HCID 14798Sodium HydroxideHCID 22497220HCID 22497220, compound

Product 1

HCID 224972496-Methoxy-1-(propan-2-yl)-1H-indole-3-carboxylic acidYield 71%

Conditions

Temperature
25 °C

Procedure

A solution of 2,2,2-trifluoro-1-(1-isopropyl-6-methoxy-1H-indol-3-yl)-ethanone (950 mg, 3.33 mmol) in a 20% aqueous sodium hydroxide solution (12 mL) was heated at 105° C. for 18 h. At this time, the reaction was cooled to 25° C., partitioned between water (50 mL) and ethyl acetate (50 mL), and treated with a 1N aqueous hydrochloric acid solution (35 mL). The organic layer was dried over magnesium sulfate, filtered, and concentrated in vacuo. The resulting solids were collected by filtration, washed with petroleum ether, and dried in vacuo to afford 1-isopropyl-6-methoxy-1H-indole-3-carboxylic acid (553 mg, 71%) as orange needles: mp 162-163° C.; EI-HRMS m/e calcd for C13H15NO3 (M+) 233.1052, found 233.1056.

Workup

  1. custompartitioned between water (50 mL) and ethyl acetate (50 mL)
  2. additiontreated with a 1N aqueous hydrochloric acid solution (35 mL)
  3. dry with materialThe organic layer was dried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. filtrationThe resulting solids were collected by filtration
  7. washwashed with petroleum ether
  8. customdried in vacuo

Sources & evidence

ORD record
ord-b114171829dd4a9590191ac37c0a1a5b
Source dataset
uspto-grants-2005_04
Patent number
US06881844B2

Reaction notes

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