N,N-Dimethylaniline → HCID 21294782, compound

HRID 35685Notes

Reaction equation

HRID 35685 reaction equation
[CH:1]1([C:4](Cl)=[O:5])[CH2:3][CH2:2]1.CN(C)C1C=CC=CC=1.[Cl:16][C:17]1[CH:26]=[CH:25][C:24]2[NH:23][CH2:22][C:21]3[CH:27]=[N:28][N:29]([CH3:30])[C:20]=3[C:19]=2[CH:18]=1>CN(C)C1C=CN=CC=1.C(Cl)(Cl)Cl>[Cl:16][C:17]1[CH:26]=[CH:25][C:24]2[N:23]([C:4]([CH:1]3[CH2:3][CH2:2]3)=[O:5])[CH2:22][C:21]3[CH:27]=[N:28][N:29]([CH3:30])[C:20]=3[C:19]=2[CH:18]=1

Participants

6

Reactant 3

HCID 949N,N-DimethylanilineHCID 77637Cyclopropanecarbonyl chlorideHCID 135624259HCID 135624259, compound

Product 1

HCID 21294782HCID 21294782, compound

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6212ChloroformSolvent

Procedure

Cyclopropanecarbonyl chloride (1.5 ml) was addded dropwise to a mixture of N,N-dimethylaniline (2.4 ml), 4-dimethylaminopyridine (5.0 mg) and 8-chloro-4,5-dihydro-1-methyl-1H -pyrazolo[4,3-c]quinoline (2.0 g) in chloroform (20 ml) at 0° C. and the mixture was allowed to stir at that temperature for 2 hours. After the solvent was evaporated in vacuo, the residue was mixed with 5% hydrochloric acid and extracted with ethyl acetate. The extract was washed with 5% hydrochloric acid, saturated aqueous sodium hydrogen carbonate and water and then dried over magnesium sulfate. The solvent was evaported in vacuo to give light brown powder (2. 0 g), which was recrystallized from a mixture of n-hexane and ethyl acetate to afford 8-chloro-5-cyclopropylcarbonyl-4,5-dihydro-1-methyl-1H-pyrazolo[4,3-c]quinoline as colourless prisms.

Workup

  1. customAfter the solvent was evaporated in vacuo
  2. additionthe residue was mixed with 5% hydrochloric acid
  3. extractionextracted with ethyl acetate
  4. washThe extract was washed with 5% hydrochloric acid, saturated aqueous sodium hydrogen carbonate and water
  5. dry with materialdried over magnesium sulfate
  6. customto give light brown powder (2. 0 g), which
  7. customwas recrystallized from a mixture of n-hexane and ethyl acetate

Sources & evidence

ORD record
ord-7bb2681dc17d4e8fa30c761ca13157fe
Source dataset
uspto-grants-1988_08
Patent number
US04767780

Reaction notes

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