Furfurylamine → 2-Amino-3-cyano-4-furfurylaminoquinoline

HRID 2233277Notes

Reaction equation

HRID 2233277 reaction equation
[NH2:1][C:2]1[C:11]([C:12]#[N:13])=[C:10](Cl)[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[N:3]=1.[CH2:15]([NH2:21])[C:16]1[O:20][CH:19]=[CH:18][CH:17]=1>O>[NH2:1][C:2]1[C:11]([C:12]#[N:13])=[C:10]([NH:21][CH2:15][C:16]2[O:20][CH:19]=[CH:18][CH:17]=2)[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[N:3]=1

Participants

4

Reactant 2

HCID 3438FurfurylamineHCID 114811212-Amino-3-cyano4-chloroquinoline

Product 1

HCID 222737212-Amino-3-cyano-4-furfurylaminoquinolineYield 44.7%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
25 °C

Procedure

10 g of 2-amino-3-cyano-4-chloroquinoline is heated with 19 g of furfurylamine at 120° C. for 3 hours. The reaction mixture is cooled to 25° C. and mixed 6 times with 50 ml of water. The crystals are filtered off and dried. The resulting product is recrystallized from 60 ml of N,N-dimethylformamide, to obtain 5.8 g of the title compound, m.p.: 206° C.

Workup

  1. filtrationThe crystals are filtered off
  2. customdried
  3. customThe resulting product is recrystallized from 60 ml of N,N-dimethylformamide

Sources & evidence

ORD record
ord-b5fbc5f131bf4a329e0d791f5f02bcb6
Source dataset
uspto-grants-2010_05
Patent number
US07709489B2

Reaction notes

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