Dimethylformamide → 3-formyl-N-methyl-1H-indole-2-carboxamide

HRID 1362431Notes

Reaction equation

HRID 1362431 reaction equation
C(Cl)(=O)[C:2](Cl)=[O:3].CN(C)C=O.ClCCl.[CH3:15][NH:16][C:17]([C:19]1[NH:20][C:21]2[C:26]([CH:27]=1)=[CH:25][CH:24]=[CH:23][CH:22]=2)=[O:18]>O>[CH:2]([C:27]1[C:26]2[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=2)[NH:20][C:19]=1[C:17]([NH:16][CH3:15])=[O:18])=[O:3]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 6344DichloromethaneHCID 65578Oxalyl chlorideHCID 12461785N-methyl-1H-indole-2-carboxamide

Product 1

HCID 592775763-formyl-N-methyl-1H-indole-2-carboxamideYield 50.2%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Oxalyl chloride (2.6 mL, 30 mmol) was added drop-wise to an ice-cooled solution of dimethylformamide (34 mL) and dichloromethane (90 mL), then N-methyl-1H-indole-2-carboxamide (3.51 g, 20 mmol) was added and the mixture stirred at rt for 1 h. Water was added and the resulting precipitate filtered, washed with water and diethyl ether. The product was dried to afford the title compound (2.03 g, 50%). 1H NMR (300 MHz, DMSO-d6) δ 12.58 (s, 1H), 10.2 (s, 1H), 9.51 (s, 1H), 8.26 (d, J=7.5 Hz, 1H), 7.66 (d, J=8.6 Hz, 1H), 7.47-7.10 (m, 2H), 2.73 (d, J=4.6 Hz, 3H).

Workup

  1. filtrationthe resulting precipitate filtered
  2. washwashed with water and diethyl ether
  3. customThe product was dried

Sources & evidence

ORD record
ord-e3954f9be92b4895ae52cbfaf767a960
Source dataset
uspto-grants-2011_02
Patent number
US07879872B2

Reaction notes

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