Indole → 1H-indole-3-carboxamide

HRID 1947056Notes

Reaction equation

HRID 1947056 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH:3]=[CH:2]1.[OH2:10].C[C:12]#[N:13]>Cl>[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3]([C:12]([NH2:13])=[O:10])=[CH:2]1

Participants

5

Reactant 3

HCID 798IndoleHCID 962WaterHCID 6342Acetonitrile

Product 1

HCID 21925421H-indole-3-carboxamideYield 66%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidCatalyst

Conditions

Temperature
0 °C

Procedure

CSI (0.578 mL, 6.63 mmol) was added dropwise to a solution of indole (777 mg, 6.63 mmol) in dry CH3CN (125 mL) at 0° C., and the mixture stirred at 0° C. for 1 h. Water (10 mL) was added, with HCl (1 drop, conc. aq), and the mixture heated to 100° C. for 2 h with stirring, then stirred at RT for 2.5 h, then refrigerated over the weekend. The reaction mixture was then evaporated to dryness, recrystallized from aqueous acetonitrile, filtered, and dried under vacuum overnight to provide 1H-indole-3-carboxylic acid amide (700 mg, 66% yield).

Workup

  1. temperaturethe mixture heated to 100° C. for 2 h
  2. stirringwith stirring
  3. stirringstirred at RT for 2.5 h
  4. customThe reaction mixture was then evaporated to dryness
  5. customrecrystallized from aqueous acetonitrile
  6. filtrationfiltered
  7. customdried under vacuum overnight

Sources & evidence

ORD record
ord-929191cf45de4e72b9a61c1735a9b90f
Source dataset
uspto-grants-2013_03
Patent number
US08399462B2

Reaction notes

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