Dimethylformamide → 6-Chloro-1H-indole-3-carboxaldehyde

HRID 1642047Notes

Reaction equation

O=P(Cl)(Cl)Cl.[Cl:6][C:7]1[CH:15]=[C:14]2[C:10]([CH:11]=[CH:12][NH:13]2)=[CH:9][CH:8]=1.[OH-].[Na+].CN([CH:21]=[O:22])C>O>[Cl:6][C:7]1[CH:15]=[C:14]2[C:10]([C:11]([CH:21]=[O:22])=[CH:12][NH:13]2)=[CH:9][CH:8]=1

Participants

Conditions

Temperature: 37 °C

Procedure

This Vilsmeyer reaction was performed according to H. G. O. Becker, Organikum, pp. 364-365, Johann Ambrosius Barth Verlag, Heidelberg-Leipzig (1996). To 5 mL DMF in a three-necked flask equipped with a thermometer, 1.8 mL POCl3 was added dropwise in a temperature range between 15° C. and 20° C. Then, a solution of 1 g (6.6 mMol) of 6-chloro-1H-indole in 2 mL DMF was added dropwise in a temperature range between 20° C. and 30° C. The reaction mixture was stirred for 45 minutes at 37° C. Afterwards, the reaction mixture was poured in a mixture of 15 g ice in 10 mL water under stirring. 3.4 g NaOH in 18 mL were added between in a temperature range between 20 and 30° C. The resulting mixture was then refluxed for 5 minutes. After cooling to room temperature, the precipitate was filtered off and washed with 10 mL cold water. Crystallization from ethanol yielded 6-chloro-1H-indole-3-carbaldehyde as a white solid (1.04 g, 88%).

Workup

customThis Vilsmeyer reaction
additionwas added dropwise in a temperature range between 15° C. and 20° C
stirringunder stirring
temperatureThe resulting mixture was then refluxed for 5 minutes
temperatureAfter cooling to room temperature
filtrationthe precipitate was filtered off
washwashed with 10 mL cold water
customCrystallization from ethanol

Sources & evidence

ORD record: ord-ca9b2d26d5094cac9f878a78dbdd228a
Source dataset: uspto-grants-2012_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08119623B2

Reaction notes

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