Dimethylformamide → 1-methylindoline-5-carbaldehyde

HRID 476837Notes

Reaction equation

HRID 476837 reaction equation
P(Cl)(Cl)(Cl)=O.CN([CH:9]=[O:10])C.[CH3:11][N:12]1[C:20]2[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=2)[CH2:14][CH2:13]1>O>[CH:9]([C:17]1[CH:16]=[C:15]2[C:20](=[CH:19][CH:18]=1)[N:12]([CH3:11])[CH2:13][CH2:14]2)=[O:10]

Participants

5

Reactant 3

HCID 6228Dimethylformamide2×HCID 24813Phosphorus oxychlorideHCID 558301-Methyl-2,3-dihydro-1H-indole

Product 1

HCID 5951811-methylindoline-5-carbaldehydeYield 62%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Phosphorus oxychloride (1.23 g., 0.0080 mole) was slowly added dropwise to 5 ml. of DMF which was cooled in an ice bath. The solution was stirred for 5 minutes and to it there was added dropwise a solution of 1-methylindoline (1.0 g., 0.0075 mole) in 2 ml. of DMF. The resulting mixture was stirred in the ice bath for 5 minutes, then at room temperature for 1 hour and finally at 80° C. for 2 hours. The reaction mixture was cooled to room temperature, slowly poured into water with stirring and extracted with ethyl ether. The crude oil was chromatographed on silica gel with 80/20 (v/v) CH2Cl2 /EtOAc to yield 0.745 g. (62% yield) of 5-formyl-1-methylindoline as a yellow solid, m.p. 39°-41° C.

Workup

  1. waitat room temperature for 1 hour
  2. waitfinally at 80° C. for 2 hours
  3. stirringwith stirring
  4. extractionextracted with ethyl ether
  5. customThe crude oil was chromatographed on silica gel with 80/20 (v/v) CH2Cl2 /EtOAc
  6. customto yield 0.745 g

Sources & evidence

ORD record
ord-a54c751e915c46b48173026a3037f118
Source dataset
uspto-grants-1989_12
Patent number
US04886744

Reaction notes

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