Dimethylformamide → 1,2-Dimethyl-1H-indole-3-carboxaldehyde

HRID 225901

Reaction equation

HRID 225901 reaction equation
O=P(Cl)(Cl)Cl.[CH3:6][N:7]1[C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[CH:9]=[C:8]1[CH3:16].[OH-].[Na+].CN([CH:22]=[O:23])C>O>[CH3:6][N:7]1[C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[C:9]([CH:22]=[O:23])=[C:8]1[CH3:16]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 134081,2-DimethylindoleHCID 14798Sodium HydroxideHCID 24813Phosphorus oxychloride

Product 1

HCID 5990841,2-Dimethyl-1H-indole-3-carboxaldehydeYield 97%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A solution of POCl3 (7.0 mL, 75 mmole) in DMF (100 mL) was stirred for 5 minutes at 0° C., then 1,2-dimethylindole (10.0 g, 69 mmole) was added in one portion. The reaction was allowed to warm to RT and stirred for 4 h. The thick slurry was poured into ice water (300 mL) and the flask was rinsed with additional water (50 mL). The aqueous mixture was basified with a solution of NaOH (13.2 g, 330 mmole) in H2O (50 mL), and the thick suspension was filtered to collect the solid. This was washed with water and dried under vacuum to give the title compound (11.59 g, 97%) as an off-white solid:

Workup

  1. washthe flask was rinsed with additional water (50 mL)
  2. filtrationthe thick suspension was filtered
  3. customto collect the solid
  4. washThis was washed with water
  5. customdried under vacuum

Sources & evidence

ORD record
ord-4b1b7dedbeee41f8baa394c3b77c2a98
Source dataset
uspto-grants-2009_07
Patent number
US07557125B2

Linked notes

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