2-Chloro-N,N-dimethylethylamine → 11-Amino-4,5-dihydro-2-(2-dimethylaminoethyl)-2H-pyrazolo [3,4-a]acridine

HRID 1646214Notes

Reaction equation

HRID 1646214 reaction equation
[NH2:1][C:2]1[C:3]2[C:8]([N:9]=[C:10]3[C:15]=1[C:14]1[NH:16][N:17]=[CH:18][C:13]=1[CH2:12][CH2:11]3)=[CH:7][CH:6]=[CH:5][CH:4]=2.[H-].[Na+].[CH3:21][N:22]([CH3:26])[CH2:23][CH2:24]Cl>CN(C=O)C>[NH2:1][C:2]1[C:3]2[C:8]([N:9]=[C:10]3[C:15]=1[C:14]1=[N:16][N:17]([CH2:24][CH2:23][N:22]([CH3:26])[CH3:21])[CH:18]=[C:13]1[CH2:12][CH2:11]3)=[CH:7][CH:6]=[CH:5][CH:4]=2

Participants

5

Reactant 3

HCID 79012-Chloro-N,N-dimethylethylamine2×HCID 24758Sodium hydrideHCID 10421619HCID 10421619, compound

Product 1

HCID 1004088711-Amino-4,5-dihydro-2-(2-dimethylaminoethyl)-2H-pyrazolo [3,4-a]acridine

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 11-amino-4,5-dihydro-1H-pyrazolo[3,4-a]acridine (8.0 g) in dry DMF (240 ml) was slowly added NaH (60%)(1.69 g). The reaction was stirred at room temperature for one hour, 2-dimethylaminoethylchloride (4.64 g) was added and stirring was continued for two hours. An additional 4.64 g of 2-dimethylaminoethylchloride was added and the reaction was stirred at room temperature overnight.

Workup

  1. stirringstirring
  2. waitwas continued for two hours
  3. stirringthe reaction was stirred at room temperature overnight

Sources & evidence

ORD record
ord-c69472532dfe476c8d3c61294b38eff5
Source dataset
uspto-grants-1993_01
Patent number
US05179100

Reaction notes

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