4,7-Dichloroquinoline → HCID 54478391, compound

HRID 234699Notes

Reaction equation

HRID 234699 reaction equation
Cl[C:2]1[C:11]2[C:6](=[CH:7][C:8]([Cl:12])=[CH:9][CH:10]=2)[N:5]=[CH:4][CH:3]=1.[NH2:13][CH2:14][C:15]([NH2:18])([CH3:17])[CH3:16]>CN1CCCC1=O>[Cl:12][C:8]1[CH:7]=[C:6]2[C:11]([C:2]([NH:13][CH2:14][C:15]([CH3:17])([NH2:18])[CH3:16])=[CH:3][CH:4]=[N:5]2)=[CH:10][CH:9]=1

Participants

4

Reactant 2

HCID 68664,7-DichloroquinolineHCID 131282-Methylpropylenediamine

Product 1

HCID 54478391HCID 54478391, compound

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

52.8 g of 4,7-dichloroquinoline and 30.85 g of 1,2-diamino-2-methylpropane were stirred in 530 ml of N-methyl-2-pyrrolidone under argon at 150° C. for 5 hours. Thereafter, the solvent was evaporated in a vacuum and the residue was taken up in 1250 ml of water. After adjustment to pH 1 using conc. hydrochloric acid, the mixture was extracted once with 200 ml of ethyl acetate and twice with 100 ml of ethyl acetate each time, and subsequently treated with about 170 ml of 30% potassium hydroxide solution until the pH reached 12. Thereby, 88 g of N1 -(7-chloro-quinolin-4-yl)-2-methyl-propane-1,2-diamine separate out in crystalline form; m.p.: 169°-171° C.

Workup

  1. customThereafter, the solvent was evaporated in a vacuum
  2. extractionthe mixture was extracted once with 200 ml of ethyl acetate and twice with 100 ml of ethyl acetate each time
  3. additionsubsequently treated with about 170 ml of 30% potassium hydroxide solution until the pH
  4. customThereby, 88 g of N1 -(7-chloro-quinolin-4-yl)-2-methyl-propane-1,2-diamine separate out in crystalline form

Sources & evidence

ORD record
ord-9222e8b1929e4cc2b943163590840e84
Source dataset
uspto-grants-1997_01
Patent number
US05596002

Reaction notes

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