3,7-Dichloroquinoline-8-carbonitrile → 7-(Butylamino)-3-chloroquinoline-8-carbonitrile

HRID 1980751Notes

Reaction equation

HRID 1980751 reaction equation
[Cl:1][C:2]1[CH:3]=[N:4][C:5]2[C:10]([CH:11]=1)=[CH:9][CH:8]=[C:7](Cl)[C:6]=2[C:13]#[N:14]>C(N)CCC>[CH2:3]([NH:4][C:7]1[C:6]([C:13]#[N:14])=[C:5]2[C:10]([CH:11]=[C:2]([Cl:1])[CH:3]=[N:4]2)=[CH:9][CH:8]=1)[CH2:2][CH2:11][CH3:10]

Participants

3

Reactant 1

HCID 130907923,7-Dichloroquinoline-8-carbonitrile

Product 1

HCID 132065267-(Butylamino)-3-chloroquinoline-8-carbonitrileYield 150.5%

Reagents, catalysts & solvents 1

HCID 8007ButylamineSolvent

Procedure

44.5 g of 3,7-dichloro-8-cyanoquinoline in 200 g of n-butylamine were heated at 80° C. for 14 hours, the solution was poured onto ice water and extracted with twice 100 ml of methylene chloride, the combined extracts were dried with Na2SO4 and evaporated down, the oily residue was treated with ether, and the precipitated solid was filtered off under suction. 39 g of 7-n-butylamino-3-chloro-8-cyanoquinoline of melting point 89° C. were obtained. Yield: 75% of theory.

Workup

  1. additionthe solution was poured onto ice water
  2. extractionextracted with twice 100 ml of methylene chloride
  3. dry with materialthe combined extracts were dried with Na2SO4
  4. customevaporated down
  5. additionthe oily residue was treated with ether
  6. filtrationthe precipitated solid was filtered off under suction

Sources & evidence

ORD record
ord-dc737421c13d49a0b0b64fab089ffe41
Source dataset
uspto-grants-1985_04
Patent number
US04511393

Reaction notes

Loading…