Dimethylformamide → 3-Formyl-1H-indole-5-carbonitrile

HRID 1666797

Reaction equation

HRID 1666797 reaction equation
P(Cl)(Cl)(Cl)=O.[C:6]([C:8]1[CH:9]=[C:10]2[C:14](=[CH:15][CH:16]=1)[NH:13][CH:12]=[CH:11]2)#[N:7].[OH-].[Na+].CN([CH:22]=[O:23])C>>[CH:22]([C:11]1[C:10]2[C:14](=[CH:15][CH:16]=[C:8]([C:6]#[N:7])[CH:9]=2)[NH:13][CH:12]=1)=[O:23]

Participants

5

Reactant 4

HCID 6228Dimethylformamide2×HCID 14798Sodium Hydroxide2×HCID 24813Phosphorus oxychlorideHCID 27513Indole-5-carbonitrile

Product 1

HCID 285043-Formyl-1H-indole-5-carbonitrile

Procedure

Add phosphorous oxychloride (11.76 g, 76.67 mmol) dropwise to DMF (24.3 ml) wile maintaining the temperature at less than 10° C. Warm to ambient temperature and stir for 15 minutes at ambient temperature. Add dropwise 5-cyanoindole (10.00 g, 70.34 mmol) as a solution in DMF (30 ml) while keeping the temperature below 35°. After 1 hour, pour the reaction mixture into ice/water (300 ml) and then add 5N NaOH (54 ml) with stirring Add slowly an additional amount of 5N NaOH (19.7 ml) and then heated to 90° for 1 minute and then cooled to ambient temperature to give a precipitate. Filter the precipitate and washed with water and dry to give the title compound: mp 248-250° C. MS (ACPI): m/e 171.0 (M+1). Analysis for C10H6N2O: Calcd: C, 70.58; H, 3.55; N, 16.46. found: C, 70.41; H, 3.53; N, 16.33.

Workup

  1. temperaturewile maintaining the temperature at less than 10° C
  2. customthe temperature below 35°
  3. waitAfter 1 hour
  4. stirringwith stirring
  5. temperatureheated to 90° for 1 minute
  6. temperaturecooled to ambient temperature
  7. customto give a precipitate
  8. filtrationFilter the precipitate
  9. washwashed with water
  10. customdry

Sources & evidence

ORD record
ord-9852ff24b1fe4280abbe641ff635e925
Source dataset
uspto-grants-2011_10
Patent number
US08044090B2

Linked notes

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