Dimethylformamide → 2-(4-Methoxyphenyl)indolizine-3-carbaldehyde

HRID 65479

Reaction equation

HRID 65479 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[CH:10]=[C:11]3[N:16]([CH:17]=2)[CH:15]=[CH:14][CH:13]=[CH:12]3)=[CH:5][CH:4]=1.P(Cl)(Cl)(Cl)=O.[OH-].[Na+].CN([CH:28]=[O:29])C>>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([C:9]2[CH:10]=[C:11]3[N:16]([C:17]=2[CH:28]=[O:29])[CH:15]=[CH:14][CH:13]=[CH:12]3)=[CH:7][CH:8]=1

Participants

5

Reactant 4

HCID 6228Dimethylformamide2×HCID 14798Sodium HydroxideHCID 24813Phosphorus oxychlorideHCID 3469492-(4-Methoxyphenyl)indolizine

Product 1

HCID 38006562-(4-Methoxyphenyl)indolizine-3-carbaldehyde

Conditions

Temperature
55 °C

Procedure

A slurry of 20 g of 2-(4-methoxy phenyl) indolizine in 35 ml of DMF was added to a solution of 10 ml of phosphorus oxychloride in 30 ml of DMF at 10°-20° C. After the reaction solution was stirred at 40° for 40 min., it was added to 200 g of ice. 120 g of 25 percent sodium hydroxide solution was added and the resulting mixture was heated to 55° C., cooled, and filtered. The air-dried product weighed 23 g.

Workup

  1. temperaturecooled
  2. filtrationfiltered

Sources & evidence

ORD record
ord-1666ce83c60d41438186d8e0aae56580
Source dataset
uspto-grants-1986_09
Patent number
US04614801

Linked notes

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