3-Aminoquinoline → (2-Chloropyrimidin-4-yl)quinolin-3-ylamine

HRID 1640679Notes

Reaction equation

HRID 1640679 reaction equation
[Cl:1][C:2]1[N:7]=[C:6](Cl)[CH:5]=[CH:4][N:3]=1.[NH2:9][C:10]1[CH:11]=[N:12][C:13]2[C:18]([CH:19]=1)=[CH:17][CH:16]=[CH:15][CH:14]=2.C(N(C(C)C)C(C)C)C>CC(O)C>[Cl:1][C:2]1[N:7]=[C:6]([NH:9][C:10]2[CH:11]=[N:12][C:13]3[C:18]([CH:19]=2)=[CH:17][CH:16]=[CH:15][CH:14]=3)[CH:5]=[CH:4][N:3]=1

Participants

5

Reactant 3

HCID 113753-AminoquinolineHCID 775312,4-DichloropyrimidineHCID 81531Diisopropylethylamine

Product 1

HCID 22326846(2-Chloropyrimidin-4-yl)quinolin-3-ylamineYield 68.7%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

50 g (0.34 mol) of 2,4-dichloropyrimidine and 50 g (0.35 mol) of 3-amino-quinoline are combined and kept at the boil under reflux for 50 h in 400 ml of 2-propanol with 100 ml of ethyldiisopropylamine. The reaction mixture is poured into 3 l of ice-water, the precipitate is filtered off with suction and washed with water. The residue is recrystallised from acetone, giving 60 g of pale-grey crystals (m.p.: 140-143° C.) (2-chloropyrimidin-4-yl)quinolin-3-ylamine.

Workup

  1. filtrationthe precipitate is filtered off with suction
  2. washwashed with water
  3. customThe residue is recrystallised from acetone

Sources & evidence

ORD record
ord-4fa377dae9a74f378f1d129a4b7490a4
Source dataset
uspto-grants-2012_02
Patent number
US08114882B2

Reaction notes

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