Dimethylformamide → HCID 13490349, compound

HRID 485335Notes

Reaction equation

HRID 485335 reaction equation
CN(C)[CH:3]=[O:4].P(Cl)(Cl)(Cl)=O.[N:11]1[CH:16]=[CH:15][CH:14]=[C:13]([N:17]2[C:25]3[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=3)[CH:19]=[CH:18]2)[CH:12]=1.O.O.O.C([O-])(=O)C.[Na+]>ClCCCl.O>[N:11]1[CH:16]=[CH:15][CH:14]=[C:13]([N:17]2[C:25]3[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=3)[C:19]([CH:3]=[O:4])=[CH:18]2)[CH:12]=1

Participants

7

Reactant 4

HCID 6228DimethylformamideHCID 24813Phosphorus oxychlorideHCID 134903481-(pyridin-3-yl)-1H-indoleHCID 23665404Sodium Acetate Trihydrate

Product 1

HCID 13490349HCID 13490349, compound

Reagents, catalysts & solvents 2

HCID 111,2-DichloroethaneSolvent2×HCID 962WaterSolvent

Procedure

A solution of 2.12 ml of N,N-dimethylformamide in 20 ml of 1,2-dichloroethane is cooled to 0° and 3.1 ml of phosphorus oxychloride is added dropwise. The reaction is stirred for 10 minutes at 15° and recooled to 0° before a solution of 4.85 g of N-(3-pyridyl)indole in 10 ml of 1,2-dichloroethane is added. After 2 hours at 5°, the reaction mixture is refluxed for 15 minutes, cooled to room temperature and a solution of 18.75 g of sodium acetate trihydrate in 25 ml of water is added. After an additional 15 minutes at reflux, the organic phase is separated, washed with sodium bicarbonate and water, and dried over magnesium sulfate. Filtration, evaporation and recrystallization of the residue from methylene chloride-methanol yields N-(3-pyridyl)-indole-3-carboxaldehyde, m.p. 148°-150°.

Workup

  1. additionis added
  2. waitAfter 2 hours at 5°
  3. temperaturethe reaction mixture is refluxed for 15 minutes
  4. temperatureAfter an additional 15 minutes at reflux
  5. customthe organic phase is separated
  6. washwashed with sodium bicarbonate and water
  7. dry with materialdried over magnesium sulfate
  8. filtrationFiltration, evaporation and recrystallization of the residue from methylene chloride-methanol

Sources & evidence

ORD record
ord-e322f9da7d7d4ac1b4a8eb482f2c1432
Source dataset
uspto-grants-1985_08
Patent number
US04536505

Reaction notes

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