4,7-Dichloroquinoline → HCID 178521589, compound

HRID 617239Notes

Reaction equation

HRID 617239 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.Cl.[NH2:14][C@H:15]1[CH2:20][CH2:19][C@H:18]([OH:21])[CH2:17][CH2:16]1.C(N(CC)CC)C.[OH-].[Na+]>CN1CCCC1=O.O>[Cl:12][C:8]1[CH:7]=[C:6]2[C:11]([C:2]([NH:14][C@H:15]3[CH2:20][CH2:19][C@H:18]([OH:21])[CH2:17][CH2:16]3)=[CH:3][CH:4]=[N:5]2)=[CH:10][CH:9]=1

Participants

7

Reactant 4

HCID 68664,7-DichloroquinolineHCID 8471TriethylamineHCID 14798Sodium HydroxideHCID 178479278HCID 178479278, compound

Product 1

HCID 178521589HCID 178521589, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

414.2 g of 4,7-dichloroquinoline, 380 g of trans-4-amino-cyclohexanol hydrochloride and 255 9 of triethylamine were heated to reflux overnight in 1.05 l of 1-methyl-2-pyrrolidone under an argon atmosphere. After cooling the reaction mixture 3.8 l of water and 380 ml of 28% sodium hydroxide solution were added thereto while stirring and cooling. The separated reaction product was filtered off under suction, washed with water until the wash water was neutral and dried at 100° C./12 mbar. Yield 491 g (84.9%) of trans-N-(7-chloro-quinolin-4-yl)-4-aminocyclohexanol.

Workup

  1. additionwere added
  2. temperaturecooling
  3. customThe separated reaction product
  4. filtrationwas filtered off under suction
  5. washwashed with water until the wash water
  6. customdried at 100° C./12 mbar

Sources & evidence

ORD record
ord-249183c4f640463989fee76c7c711645
Source dataset
uspto-grants-1999_09
Patent number
US05948791

Reaction notes

Loading…