Potassium Carbonate → 1H-Indazole-1-ethanamine, N,N-dimethyl-5-nitro-

HRID 1790114Notes

Reaction equation

HRID 1790114 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]2[C:10](=[CH:11][CH:12]=1)[NH:9][N:8]=[CH:7]2)([O-:3])=[O:2].C(=O)([O-])[O-].[K+].[K+].Cl.[CH3:20][N:21]([CH3:25])[CH2:22][CH2:23]Cl>CN(C=O)C>[CH3:20][N:21]([CH3:25])[CH2:22][CH2:23][N:9]1[C:10]2[C:6](=[CH:5][C:4]([N+:1]([O-:3])=[O:2])=[CH:12][CH:11]=2)[CH:7]=[N:8]1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 215015-NitroindazoleHCID 11636816N,N-Dimethylaminoethyl chloride hydrochloride

Product 1

HCID 2157401H-Indazole-1-ethanamine, N,N-dimethyl-5-nitro-Yield 64%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

A mixture of 5-nitroindazole (2 g, 12 mmol) and potassium carbonate (5.1 g 37 mmol) in DMF (40 mL) was stirred for 30 minutes after which 2-(dimethylamino)ethylchloride hydrochloride (2.65 g 18.4 mmol) was added. The mixture was heated to 60° C. for 6 hours, cooled to room temperature and was filtered through a plug of silica gel, which was rinsed with triethylamine/ethyl acetate (1/4). The filtrate was concentrated under reduced pressure and purified by flash chromatography (silica gel, triethylamine/ethyl acetate 1/30) to provide the title compound (1.8 g, 64% yield). 1H NMR (300 MHz, DMSO-d6) ppm 2.73(t, J=6.44, 2H), 3.33 (s, 6H), 4.57 (t, J=6.44, 2H), 7.93 (m, 1H), 8.21 (m, 1H), 8.40 (m, 1H), 8.82 (m, 1H); MS (DCI/NH3) m/z 235 [M+H]+.

Workup

  1. additionwas added
  2. temperaturecooled to room temperature
  3. filtrationwas filtered through a plug of silica gel, which
  4. washwas rinsed with triethylamine/ethyl acetate (1/4)
  5. concentrationThe filtrate was concentrated under reduced pressure
  6. custompurified by flash chromatography (silica gel, triethylamine/ethyl acetate 1/30)

Sources & evidence

ORD record
ord-b75410c34124417cb5d6dff5f531fe63
Source dataset
uspto-grants-2006_07
Patent number
US07071182B2

Reaction notes

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