Sodium hydride → HCID 13093688, compound

HRID 1106248Notes

Reaction equation

HRID 1106248 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:20](=[O:21])[C:11]3=[CH:12][NH:13][C:14]4[CH:15]=[CH:16][CH:17]=[CH:18][C:19]=4[C:10]3=[N:9]2)=[CH:4][CH:3]=1.[H-].[Na+].[CH3:24][N:25]([CH3:30])[CH2:26][CH2:27][CH2:28]Cl>COCCOC>[CH3:24][N:25]([CH3:30])[CH2:26][CH2:27][CH2:28][N:13]1[C:14]2[CH:15]=[CH:16][CH:17]=[CH:18][C:19]=2[C:10]2=[N:9][N:8]([C:5]3[CH:6]=[CH:7][C:2]([Cl:1])=[CH:3][CH:4]=3)[C:20](=[O:21])[C:11]2=[CH:12]1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 669603-Chloro-N,N-dimethyl-1-propanamineHCID 178515186HCID 178515186, compound

Product 1

HCID 13093688HCID 13093688, compound

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent2×

Procedure

The mixture of 10.0 g of 2-(p-chlorophenyl)-pyrazolo-[4,3-c]quinolin-3(5H)-one, 1.8 g of 50% sodium hydride in mineral oil and 250 ml of 1,2-dimethoxyethane is stirred at 100° until dissolution. It is cooled to room temperature and 15.0 g of 3-dimethylaminopropyl chloride in 10 ml of 1,2-dimethoxyethane are added. The mixture is stirred at 150° overnight, cooled, the supernatant solution decanted off and the residue treated with said solvent, to yield the 5-(3-dimethylaminopropyl)-2-(p-chlorophenyl)-pyrazolo-[4-3-c]quinolin-3-one melting at 189°-191°. Similarly the 5-(2-dimethylaminoethyl)-analog is obtained, m.p. 184°-186°.

Workup

  1. stirringThe mixture is stirred at 150° overnight
  2. temperaturecooled
  3. customthe supernatant solution decanted off
  4. additionthe residue treated with said solvent

Sources & evidence

ORD record
ord-21db895836d34d2f859ee569dcd04c3b
Source dataset
uspto-grants-1982_01
Patent number
US04312870

Reaction notes

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