Ethanol → Ethyl 5-cyanoindole-2-carboxylate

HRID 1512736Notes

Reaction equation

HRID 1512736 reaction equation
S(Cl)(Cl)=O.[C:5]([C:7]1[CH:8]=[C:9]2[C:13](=[CH:14][CH:15]=1)[NH:12][C:11]([C:16]([OH:18])=[O:17])=[CH:10]2)#[N:6].[CH2:19](O)[CH3:20]>>[C:5]([C:7]1[CH:8]=[C:9]2[C:13](=[CH:14][CH:15]=1)[NH:12][C:11]([C:16]([O:18][CH2:19][CH3:20])=[O:17])=[CH:10]2)#[N:6]

Participants

4

Reactant 3

HCID 702EthanolHCID 24386Thionyl Chloride2×HCID 71446255-cyano-1H-indole-2-carboxylic Acid

Product 1

HCID 4714953Ethyl 5-cyanoindole-2-carboxylate

Procedure

Thionyl chloride (1 mL) was added to a solution of 5-cyano-1H-indole-2-carboxylic acid (D20) (1.1 g) in ethanol (120 mL) at RT. The resulting solution was heated to reflux and stirred when refluxing for 20 hours. Another portion of thionyl chloride (0.5 mL) was added. The reaction mixture was refluxed for 2 hours. The solvent was evaporated to afford ethyl 5-cyano-1H-indole-2-carboxylate (D21) (0.9 g) as a light green solid. MS (ES): C12H10N2O2 requires 214; found 215.2 (M+H+)

Workup

  1. temperatureThe resulting solution was heated
  2. temperatureto reflux
  3. temperaturerefluxing for 20 hours
  4. temperatureThe reaction mixture was refluxed for 2 hours
  5. customThe solvent was evaporated

Sources & evidence

ORD record
ord-a1c945a4c39440afba23b68eca865fbb
Source dataset
uspto-grants-2012_07
Patent number
US08217028B2

Reaction notes

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