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

HRID 2228740Notes

Reaction equation

HRID 2228740 reaction equation
P(Cl)(Cl)(Cl)=O.[NH:6]1[C:14]2[C:9](=[CH:10][C:11]([C:15]#[N:16])=[CH:12][CH:13]=2)[CH:8]=[CH:7]1.CN(C)[CH:19]=[O:20]>>[CH:19]([C:8]1[C:9]2[C:14](=[CH:13][CH:12]=[C:11]([C:15]#[N:16])[CH:10]=2)[NH:6][CH:7]=1)=[O:20]

Participants

4

Reactant 3

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

Product 1

HCID 285043-Formyl-1H-indole-5-carbonitrileYield 84%

Procedure

Phosphoryl chloride (4.24 ml, 45.48 mmol) was added dropwise to dimethylformamide (3.52 ml, 45.48 mmol) and stirred for 30 mins at room temperature. A solution of 1H-indole-5-carbonitrile (5.39 g, 37.9 mmol) in dimethylformamide (10 ml) was added dropwise. A solid precipitated, further dimethylformamide (10 ml) was added to aid stirring and the reaction mixture was then stirred at room temperature for 3 hr. Water was added to quench the reaction mixture which was then stirred for 18 hr. The stirring was stopped and the reaction mixture was left to stand, after 24 hr a pink solid had precipitated in the organic layer. The layers were separated and organic layer filtered, washed with water and dried to give the desired product (5.44 g, 84%). 1H NMR (DMSO) δ 7.60-7.80 (m, 2H), 8.20-8.30 (m, 2H), 10.00 (s, 1H), 12.20-12.35 (s, br, 1H).

Workup

  1. customA solid precipitated
  2. additionfurther dimethylformamide (10 ml) was added to aid
  3. stirringstirring
  4. stirringthe reaction mixture was then stirred at room temperature for 3 hr
  5. additionWater was added
  6. customto quench the reaction mixture which
  7. stirringwas then stirred for 18 hr
  8. waitthe reaction mixture was left
  9. waitto stand, after 24 hr
  10. customa pink solid had precipitated in the organic layer
  11. customThe layers were separated
  12. filtrationorganic layer filtered
  13. washwashed with water
  14. customdried

Sources & evidence

ORD record
ord-6c52750558df41c1a5214fe3ebc05d7f
Source dataset
uspto-grants-2002_07
Patent number
US06417203B1

Reaction notes

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