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

HRID 555702Notes

Reaction equation

HRID 555702 reaction equation
[Cl:1][C:2]1[CH:10]=[C:9]2[C:5]([CH:6]=[CH:7][NH:8]2)=[CH:4][CH:3]=1.O=P(Cl)(Cl)Cl.CN([CH:19]=[O:20])C>>[Cl:1][C:2]1[CH:10]=[C:9]2[C:5]([C:6]([CH:19]=[O:20])=[CH:7][NH:8]2)=[CH:4][CH:3]=1

Participants

4

Reactant 3

HCID 6228DimethylformamideHCID 24813Phosphorus oxychlorideHCID 871116-Chloroindole

Product 1

HCID 126146696-Chloro-1H-indole-3-carboxaldehyde

Conditions

Temperature
45 °C

Procedure

A mixture of 6-chloro-1H-indole (2.0 g, 13.2 mmol) and POCl3 (1.34 mL, 14.5 mmol) in DMF (5 mL) is heated at 45° C. for 1 h. After completion, the reaction mixture is quenched with aqueous NaHCO3, Et2O is added and the organic layer is washed with brine, dried over MgSO4 and evaporated in vacuo. Silica gel flash chromatography of the residue affords the title compound as a colorless powder; ES-MS: M+=179.9; HPLC: AtRet=3.74 min.

Workup

  1. customAfter completion, the reaction mixture is quenched with aqueous NaHCO3, Et2O
  2. additionis added
  3. washthe organic layer is washed with brine
  4. dry with materialdried over MgSO4
  5. customevaporated in vacuo

Sources & evidence

ORD record
ord-d5b0489241c14f91971843cdcb117666
Source dataset
uspto-grants-2011_11
Patent number
US08053457B2

Reaction notes

Loading…