Dimethylformamide → 7-Fluoro-1H-indole-3-carbaldehyde

HRID 1494430Notes

Reaction equation

HRID 1494430 reaction equation
P(Cl)(Cl)(Cl)=O.[F:6][C:7]1[CH:8]=[CH:9][CH:10]=[C:11]2[C:15]=1[NH:14][CH:13]=[CH:12]2.[OH-].[Na+].CN([CH:21]=[O:22])C>O>[F:6][C:7]1[CH:8]=[CH:9][CH:10]=[C:11]2[C:15]=1[NH:14][CH:13]=[C:12]2[CH:21]=[O:22]

Participants

6

Reactant 4

HCID 6228Dimethylformamide2×HCID 14798Sodium HydroxideHCID 24813Phosphorus oxychlorideHCID 27745047-Fluoro-1H-indole

Product 1

HCID 221391207-Fluoro-1H-indole-3-carbaldehyde

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Phosphoryl chloride (2.0 ml) was added to DMF (3 ml) under nitrogen at 0° and to this mixture was added 7-fluoroindole (2.1 g) in dry DMF (4 ml). The mixture was stirred for 1h, 5N sodium hydroxide solution (50 ml) was added, and stirring was continued at 50° for 1h. The mixture was then diluted with water (200 ml) and extracted with ethyl acetate (2×200 ml). The combined, dried organic extracts were evaporated in vacuo to give the title compound (2.07 g), m.p. 203°-205°.

Workup

  1. additionwas added
  2. extractionextracted with ethyl acetate (2×200 ml)
  3. customdried organic extracts were evaporated in vacuo

Sources & evidence

ORD record
ord-fa12bf155614454f83032b68e2a4919e
Source dataset
uspto-grants-1991_06
Patent number
US05026722

Reaction notes

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