Water → HCID 23355238, compound

HRID 234689Notes

Reaction equation

HRID 234689 reaction equation
Cl.Cl[CH2:3][CH2:4][NH:5][C:6]1[C:15]2[C:10](=[CH:11][C:12]([Cl:16])=[CH:13][CH:14]=2)[N:9]=[CH:8][CH:7]=1.O.[OH-].[Na+]>CC1CCCNC1>[Cl:16][C:12]1[CH:11]=[C:10]2[C:15]([C:6]([NH:5][CH2:4][CH2:3][N:9]3[CH2:8][CH2:7][CH2:6][CH:15]([CH3:14])[CH2:10]3)=[CH:7][CH:8]=[N:9]2)=[CH:14][CH:13]=1

Participants

5

Reactant 3

HCID 962WaterHCID 14798Sodium HydroxideHCID 23355222HCID 23355222, compound

Product 1

HCID 23355238HCID 23355238, compoundYield 64.3%

Reagents, catalysts & solvents 1

HCID 790813-MethylpiperidineSolvent

Procedure

2.5 g of N-(2-chloroethyl)-7-chloro-4-quinolinamine hydrochloride in 25 ml of 3-methylpiperidine were held at 100° C. in a sealed tube for 24 hours. Thereafter, 100 ml of water were added, the mixture is adjusted to pH 12 by means of concentrated sodium hydroxide solution and extracted three times with 50 ml of ethyl acetate each time. The combined extracts were washed with a small amount of water and concentrated. The residue was recrystallized from 80 ml of acetone. 0.88 g of colourless crystals, m.p.: 148°-151° C., was obtained.

Workup

  1. extractionextracted three times with 50 ml of ethyl acetate each time
  2. washThe combined extracts were washed with a small amount of water
  3. concentrationconcentrated
  4. customThe residue was recrystallized from 80 ml of acetone

Sources & evidence

ORD record
ord-1a40979f43e34f1ab5ba335d8b58d90b
Source dataset
uspto-grants-1997_01
Patent number
US05596002

Reaction notes

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