2-Chloro-N,N-dimethylethylamine → N,N-Dimethyl-2-(6-nitro-1H-indazol-1-yl)ethan-1-amine

HRID 1003269Notes

Reaction equation

HRID 1003269 reaction equation
CC([O-])(C)C.[K+].[N+:7]([C:10]1[CH:18]=[C:17]2[C:13]([CH:14]=[N:15][NH:16]2)=[CH:12][CH:11]=1)([O-:9])=[O:8].Cl[CH2:20][CH2:21][N:22]([CH3:24])[CH3:23].C(=O)([O-])[O-].[Na+].[Na+]>O1CCCC1.C1(C)C=CC=CC=1.C(OCC)(=O)C>[CH3:23][N:22]([CH3:24])[CH2:21][CH2:20][N:16]1[C:17]2[C:13](=[CH:12][CH:11]=[C:10]([N+:7]([O-:9])=[O:8])[CH:18]=2)[CH:14]=[N:15]1

Participants

8

Reactant 4

HCID 79012-Chloro-N,N-dimethylethylamineHCID 10340Sodium CarbonateHCID 242396-NitroindazoleHCID 23665647Potassium tert-butoxide

Product 1

HCID 22036583N,N-Dimethyl-2-(6-nitro-1H-indazol-1-yl)ethan-1-amine

Reagents, catalysts & solvents 3

HCID 1140TolueneSolventHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

0.11 mol of potassium tert-butylate is added to a solution of 0.11 mol (20 g) of 6-nitroindazole in 400 ml of tetrahydrofuran. After total dissolution, a solution of 0.24 mol (27 g) of 2-chloroethyl-N,N-dimethylamine in 300 ml of toluene is added. The reaction medium is heated at reflux for 3 hours. After cooling, 300 ml of a 10% sodium carbonate solution are added. The mixture is diluted with ethyl acetate and decanted, and the aqueous phase is extracted with dichloromethane. After concentration of the organic phases, the residue is purified by chromatography on silica gel using a dichloromethane/methanol mixture (98/2) as eluant to yield the expected compound.

Workup

  1. dissolutionAfter total dissolution
  2. temperatureThe reaction medium is heated
  3. temperatureat reflux for 3 hours
  4. temperatureAfter cooling
  5. customdecanted
  6. extractionthe aqueous phase is extracted with dichloromethane
  7. customAfter concentration of the organic phases, the residue is purified by chromatography on silica gel using a dichloromethane/methanol mixture (98/2) as eluant

Sources & evidence

ORD record
ord-239fd13bfe06424f935cfc98e9f6c626
Source dataset
uspto-grants-2000_04
Patent number
US06046205

Reaction notes

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