1,1-Dichloroethane → HCID 67506468, compound

HRID 2105471Notes

Reaction equation

HRID 2105471 reaction equation
[NH2:1][C:2]1[CH:3]=[N:4][C:5]2[C:10]([C:11]=1[Cl:12])=[CH:9][CH:8]=[CH:7][CH:6]=2.[CH:13]1([C:19](Cl)=[O:20])[CH2:18][CH2:17][CH2:16][CH2:15][CH2:14]1.ClC(Cl)C>ClCCl>[Cl:12][C:11]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[N:4]=[CH:3][C:2]=1[NH:1][C:19]([CH:13]1[CH2:18][CH2:17][CH2:16][CH2:15][CH2:14]1)=[O:20]

Participants

5

Reactant 3

HCID 63651,1-DichloroethaneHCID 75938Cyclohexanecarbonyl chlorideHCID 8173324-chloroquinolin-3-amine

Product 1

HCID 67506468HCID 67506468, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
90 °C

Procedure

Under a nitrogen atmosphere, a mixture of 3-amino-4-chloroquinoline (8.00 g, 1 eq), cyclohexanecarbonyl chloride (18.2 mL, 3 eq) and anhydrous dichloroethane (150 mL) was heated at 90° C. for 23 hours. The reaction mixture was diluted with dichloromethane, washed sequentially with saturated aqueous potassium carbonate, water, and brine, dried over sodium sulfate, filtered, and then concentrated under reduced pressure. The residue was triturated with hexanes to provide a solid. The solid was combined with hexanes, stirred for 30 minutes, isolated by filtration, rinsed with hexanes, and then dried to provide 11.9 g of N-(4-chloroquinolin-3-yl)cyclohexanecarboxamide.

Workup

  1. washwashed sequentially with saturated aqueous potassium carbonate, water, and brine
  2. dry with materialdried over sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was triturated with hexanes
  6. customto provide a solid
  7. customisolated by filtration
  8. washrinsed with hexanes
  9. customdried

Sources & evidence

ORD record
ord-df5beb12beb0488db1095f0b7425eb11
Source dataset
uspto-grants-2009_08
Patent number
US07579359B2

Reaction notes

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