Chloroacetonitrile → Ethyl 7-cyanomethoxy-1-methyl-4-trifluoromethyl-2-indolecarboxylate

HRID 565065Notes

Reaction equation

HRID 565065 reaction equation
[OH:1][C:2]1[CH:3]=[CH:4][C:5]([C:17]([F:20])([F:19])[F:18])=[C:6]2[C:10]=1[N:9]([CH3:11])[C:8]([C:12]([O:14][CH2:15][CH3:16])=[O:13])=[CH:7]2.C(=O)([O-])[O-].[K+].[K+].Cl[CH2:28][C:29]#[N:30]>CN(C)C=O>[C:29]([CH2:28][O:1][C:2]1[CH:3]=[CH:4][C:5]([C:17]([F:20])([F:18])[F:19])=[C:6]2[C:10]=1[N:9]([CH3:11])[C:8]([C:12]([O:14][CH2:15][CH3:16])=[O:13])=[CH:7]2)#[N:30]

Participants

5

Reactant 3

HCID 7856ChloroacetonitrileHCID 11430Potassium CarbonateHCID 21194312Ethyl 7-hydroxy-1-methyl-4-trifluoromethyl-2-indolecarboxylate

Product 1

HCID 21194660Ethyl 7-cyanomethoxy-1-methyl-4-trifluoromethyl-2-indolecarboxylateYield 99.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 4.00 g (13.9 mmol) of ethyl 7-hydroxy-1-methyl-4-trifluoromethyl-2-indolecarboxylate, 4.23 g (30.6 mmol) of potassium carbonate, 1.26 g (16.7 mmol) of chloroacetonitrile and 60 ml of dimethylformamide was stirred at room temperature for 2 hours. Insoluble matters were filtered off. The filtrate was poured onto ice water followed by extraction with diethyl ether. The extract was washed with water and then dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure and the resulting residue was purified by silica gel column chromatography to give 4.50 g of ethyl 7-cyanomethoxy-1-methyl-4-trifluoromethyl-2-indolecarboxylate.

Workup

  1. filtrationInsoluble matters were filtered off
  2. additionThe filtrate was poured onto ice water
  3. extractionfollowed by extraction with diethyl ether
  4. washThe extract was washed with water
  5. dry with materialdried over anhydrous magnesium sulfate
  6. distillationThe solvent was distilled off under reduced pressure
  7. customthe resulting residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-a88a7b2b086147939aa801f9e69a3f2a
Source dataset
uspto-grants-2001_01
Patent number
US06169107A

Reaction notes

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