Ethanol → HCID 12854870, compound

HRID 1156576Notes

Reaction equation

HRID 1156576 reaction equation
[CH2:1]([C:3]1[C:7]([C:8]2[NH:9][C:10]3[C:15]([C:16]=2[CH2:17]N(C)C)=[CH:14][CH:13]=[CH:12][CH:11]=3)=[C:6]([CH3:21])[O:5][N:4]=1)[CH3:2].[C-]#[N:23].[Na+].[CH2:25]([OH:27])C>O>[CH2:1]([C:3]1[C:7]([C:8]2[NH:9][C:10]3[C:15]([C:16]=2[CH2:17][C:25]([NH2:23])=[O:27])=[CH:14][CH:13]=[CH:12][CH:11]=3)=[C:6]([CH3:21])[O:5][N:4]=1)[CH3:2]

Participants

5

Reactant 3

HCID 702EthanolHCID 8929Sodium CyanideHCID 12854868HCID 12854868, compound

Product 1

HCID 12854870HCID 12854870, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 24.8 g. (0.088 mole) of 2-(3-ethyl-5-methyl-4-isoxazolyl)-3-(dimethylaminomethyl)-indole and 23 g. (0.47 mole) of sodium cyanide in 175 ml. ethanol and 50 ml. water are refluxed for 80 hours. The mixture is then cooled and poured onto water, stirred for 1/2 hour and filtered to yield 2-(3-ethyl-5-methyl-4-isoxazolyl)-3-indole acetamide; m.p. 194° to 195° C. The filtrate, which contains the sodium salt of 2-(3-ethyl-5-methyl-4-isoxazolyl)-3-indole acetic acid is evaporated to remove ethanol and acidified with cold 12 N hydrochloric acid and the precipitate filtered to give 2-(3-ethyl-5-methyl-4-isoxazolyl)-3-indole acetic acid; m.p. 194° to 197° C.

Workup

  1. additionA mixture of 24.8 g
  2. temperatureThe mixture is then cooled
  3. additionpoured onto water
  4. filtrationfiltered

Sources & evidence

ORD record
ord-1ee62fd4a4a5499d92f5a4fa3d17f775
Source dataset
uspto-grants-1982_06
Patent number
US04336378

Reaction notes

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