ethyl 4,6-dichloro-1-methyl-1H-indole-2-carboxylate → N,1-dimethylindole-2-carboxamide

HRID 18271

Reaction equation

HRID 18271 reaction equation
Cl[C:2]1[CH:10]=[C:9](Cl)[CH:8]=[C:7]2[C:3]=1[CH:4]=[C:5]([C:13]([O:15]CC)=O)[N:6]2[CH3:12].[CH3:18][NH2:19].CO>>[CH3:18][NH:19][C:13]([C:5]1[N:6]([CH3:12])[C:7]2[C:3]([CH:4]=1)=[CH:2][CH:10]=[CH:9][CH:8]=2)=[O:15]

Participants

3

Reactant 2

HCID 22139053ethyl 4,6-dichloro-1-methyl-1H-indole-2-carboxylateHCID 57454252Monomethylamine methanol

Product 1

HCID 12303315N,1-dimethylindole-2-carboxamideYield 99%

Conditions

Temperature
50 °C

Procedure

A suspension of ethyl 4,6-dichloro-1-methyl-1H-indole-2-carboxylate (1.06 g, 3.90 mmole) in 2.0 M CH3NH2/CH3OH (40 mL) in a sealed pressure bottle was heated in an oil bath preset at 50° C. A homogeneous solution formed within 2.5 hr. The reaction was kept at 50° C. for 17.5 hr, during which time a solid precipitated. The mixture was cooled to RT and poured into H2O (40 mL). The resulting mixture was concentrated on the rotavap to remove the methanol, and the solid was collected by suction filtration. This was washed with plenty of H2O and dried in high vacuum at 45-50° C. to afford the title compound (0.99 g, 99%) as an off-white solid: 1H NMR (400 MHz, CDCl3) δ 7.29 (s, 1 H), 7.16 (d, J=1.5 Hz, 1 H), 6.86 (s, 1 H), 6.21 (br s, 1 H), 4.02 (s, 3 H), 3.02 (d, J=4.9 Hz, 3 H); MS (ES) m/e 257 and 259 (M+H)+.

Workup

  1. customA homogeneous solution formed within 2.5 hr
  2. customa solid precipitated
  3. temperatureThe mixture was cooled to RT
  4. additionpoured into H2O (40 mL)
  5. concentrationThe resulting mixture was concentrated on the rotavap
  6. customto remove the methanol
  7. filtrationthe solid was collected by suction filtration
  8. washThis was washed with plenty of H2O
  9. customdried in high vacuum at 45-50° C.

Sources & evidence

ORD record
ord-aa345c6a0d774baf803d5bbb2876f9e1
Source dataset
uspto-grants-2010_06
Patent number
US07741339B2

Linked notes

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