Sodium Hydroxide → 5-Methoxy-6-(trifluoromethyl)indoline

HRID 840543Notes

Reaction equation

HRID 840543 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][C:11]=1[C:12]([F:15])([F:14])[F:13])[NH:8][CH:7]=[CH:6]2.C([BH3-])#N.[Na+].[OH-].[Na+]>C(O)(=O)C.O>[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][C:11]=1[C:12]([F:15])([F:13])[F:14])[NH:8][CH2:7][CH2:6]2

Participants

6

Reactant 3

HCID 14798Sodium HydroxideHCID 5003444Sodium cyanoborohydrideHCID 108225525-Methoxy-6-(trifluoromethyl)-1H-indole

Product 1

HCID 112067135-Methoxy-6-(trifluoromethyl)indolineYield 99%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 962WaterSolvent

Procedure

The indole (D2) (67.63 g, 0.315 mol) in glacial acetic acid (500 ml) was treated with sodium cyanoborohydride (40 g, 0.637 mol) portionwise at room temperature with stirring. After 3 h at room temperature the reaction mixture was diluted with water (500 ml) and basified with 40% aqueous NaOH with cooling. The mixture was then extracted with dichloromethane (3×500 ml) and the combined extracts were dried (Na2SO4) and evaporated to give the title compound (67.73 g, 99%) as an off-white solid.

Workup

  1. temperaturewith cooling
  2. extractionThe mixture was then extracted with dichloromethane (3×500 ml)
  3. dry with materialthe combined extracts were dried (Na2SO4)
  4. customevaporated

Sources & evidence

ORD record
ord-073aa94d19c44708b81e9e62e6c7d586
Source dataset
uspto-grants-2002_04
Patent number
US06369060B1

Reaction notes

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