Water → Ethyl 6-chloro-3-formyl-1H-indole-2-carboxylate

HRID 1865920Notes

Reaction equation

HRID 1865920 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[NH:7][C:8]2[C:13]([CH:14]=1)=[CH:12][CH:11]=[C:10]([Cl:15])[CH:9]=2)=[O:5])[CH3:2].P(Cl)(Cl)(Cl)=O.O.[OH-].[Na+].CN([CH:27]=[O:28])C>>[CH2:1]([O:3][C:4]([C:6]1[NH:7][C:8]2[C:13]([C:14]=1[CH:27]=[O:28])=[CH:12][CH:11]=[C:10]([Cl:15])[CH:9]=2)=[O:5])[CH3:2]

Participants

6

Reactant 5

HCID 962WaterHCID 6228DimethylformamideHCID 14798Sodium HydroxideHCID 24813Phosphorus oxychlorideHCID 7015027Ethyl 6-chloroindole-2-carboxylate

Product 1

HCID 4591751Ethyl 6-chloro-3-formyl-1H-indole-2-carboxylate

Conditions

Temperature
60 °C

Procedure

To a stirred solution of 2.36 g (0.011 mol) of 6-chloro-1H-indole-2-carboxylic acid ethyl ester in DMF (20 ml) was added phosphorus oxychloride (1.08 ml, 0.012 mol) at RT. The solution was heated at 60° C. for 2 hours, then cooled to RT, and poured into water. The ph was adjusted to 7 by careful addition of aq. NaOH 2N. The resulting brown precipitate was collected by filtration and dried over night in a vacuum oven (50° C.). The title compound was obtained as light brown solid, 2.05 g (77%).

Workup

  1. temperaturecooled to RT
  2. filtrationThe resulting brown precipitate was collected by filtration
  3. customdried over night in a vacuum oven (50° C.)

Sources & evidence

ORD record
ord-922e35a1652d4c3786365db6252b82d6
Source dataset
uspto-grants-2009_12
Patent number
US07629353B2

Reaction notes

Loading…