Phosphorus oxychloride → methyl 3-formyl-1H-indole-4-carboxylate

HRID 1284027Notes

Reaction equation

HRID 1284027 reaction equation
CN([CH:9]=[O:10])C1C=CC=CC=1.P(Cl)(Cl)(Cl)=O.[CH3:16][O:17][C:18]([C:20]1[C:21]2[CH:22]=[CH:23][NH:24][C:25]=2[CH:26]=[CH:27][CH:28]=1)=[O:19].C([O-])(=O)C.[Na+]>C(Cl)CCl>[CH3:16][O:17][C:18]([C:20]1[C:21]2[C:22]([CH:9]=[O:10])=[CH:23][NH:24][C:25]=2[CH:26]=[CH:27][CH:28]=1)=[O:19]

Participants

6

Reactant 4

HCID 24813Phosphorus oxychlorideHCID 66737N-MethylformanilideHCID 517045Sodium AcetateHCID 2733668methyl 1H-indole-4-carboxylate

Product 1

HCID 12396096methyl 3-formyl-1H-indole-4-carboxylate

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent2×

Procedure

To a stirred mixture of N-methylformanilide (15.6 g) and phosphorus oxychloride (17.7 g) is added ethylene dichloride (75 g) followed by 4-indolecarboxylic acid methyl ester (17.5 g), described by F. C. Uhle, J. Amer. Chem. Soc., 71, 761 (1949). The reaction mixture is stirred at room temperature for 11/2 hr., then at 45° - 50°C for 30 minutes more. The mixture is now poured into a solution of 75 g of sodium acetate in 150 ml of ice-water. More ethylene dichloride is added. The layers are separated and the organic phase is washed with water, dried (Na2SO4) and evaporated under reduced pressure. The brown residue is treated repeatedly with boiling water from which the title compound separates on cooling. The title compound has mp 135°C.

Workup

  1. wait, then at 45° - 50°C for 30 minutes more
  2. customThe layers are separated
  3. washthe organic phase is washed with water
  4. dry with materialdried (Na2SO4)
  5. customevaporated under reduced pressure
  6. additionThe brown residue is treated repeatedly with boiling water from which the title compound separates
  7. temperatureon cooling

Sources & evidence

ORD record
ord-02049628775646969f3b4d8f3c9cc61c
Source dataset
uspto-grants-1976_08
Patent number
US03978066

Reaction notes

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