Sodium Hydroxide → HCID 22497217, compound

HRID 1816096Notes

Reaction equation

HRID 1816096 reaction equation
FC(F)(F)[C:3]([C:5]1[C:13]2[C:8](=[CH:9][C:10]([N+:14]([O-:16])=[O:15])=[CH:11][CH:12]=2)[N:7]([CH:17]([CH3:19])[CH3:18])[CH:6]=1)=[O:4].[OH-:22].[Na+]>>[CH:17]([N:7]1[C:8]2[C:13](=[CH:12][CH:11]=[C:10]([N+:14]([O-:16])=[O:15])[CH:9]=2)[C:5]([C:3]([OH:4])=[O:22])=[CH:6]1)([CH3:19])[CH3:18]

Participants

3

Reactant 2

HCID 14798Sodium HydroxideHCID 22497243HCID 22497243, compound

Product 1

HCID 22497217HCID 22497217, compoundYield 99%

Conditions

Temperature
25 °C

Procedure

A solution of 2,2,2-trifluoro-1-(1-isopropyl-6-nitro-1H-indol-3-yl)-ethanone (525 mg, 1.75 mmol) in a 20% aqueous sodium hydroxide solution (10 mL) was heated at 1110° C. for 2 h. At this time, the reaction was cooled to 25° C., partitioned between water (75 mL) and ethyl acetate (75 mL), and treated with a 1N aqueous hydrochloric acid solution (25 mL). The organic layer was washed with water (1×50 mL) and a saturated aqueous sodium chloride solution (1×50 mL), dried over magnesium sulfate, filtered, and concentrated in vacuo to afford 1-isopropyl-6-nitro-1H-indole-3-carboxylic acid (436 mg, 99%) as a yellow solid: mp 242-243° C.; EI-HRMS m/e calcd for C12H12N2O4 (M+) 248.0797, found 248.0796.

Workup

  1. custompartitioned between water (75 mL) and ethyl acetate (75 mL)
  2. additiontreated with a 1N aqueous hydrochloric acid solution (25 mL)
  3. washThe organic layer was washed with water (1×50 mL)
  4. dry with materiala saturated aqueous sodium chloride solution (1×50 mL), dried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-238d8a449199410aaf109f0bc2645ac5
Source dataset
uspto-grants-2005_04
Patent number
US06881844B2

Reaction notes

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