4-Chloro-3-nitroquinoline → 4-{[(3-nitroquinolin-4-yl)amino]methyl}tetrahydro-2H-pyran-4-ol

HRID 44716

Reaction equation

HRID 44716 reaction equation
Cl[C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[N:5]=[CH:4][C:3]=1[N+:12]([O-:14])=[O:13].[NH2:15][CH2:16][C:17]1([OH:23])[CH2:22][CH2:21][O:20][CH2:19][CH2:18]1>O>[N+:12]([C:3]1[CH:4]=[N:5][C:6]2[C:11]([C:2]=1[NH:15][CH2:16][C:17]1([OH:23])[CH2:22][CH2:21][O:20][CH2:19][CH2:18]1)=[CH:10][CH:9]=[CH:8][CH:7]=2)([O-:14])=[O:13]

Participants

4

Reactant 2

HCID 112758084-Chloro-3-nitroquinolineHCID 436087544-(Aminomethyl)oxan-4-ol

Product 1

HCID 575153954-{[(3-nitroquinolin-4-yl)amino]methyl}tetrahydro-2H-pyran-4-olYield 90%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

4-Chloro-3-nitroquinoline (12.0 g, 57.5 mmol) and was reacted with 4-(aminomethyl)tetrahydro-2H-pyran-4-ol (11.3 g, 86.3 mmol) according to the method described in Part C of Example 9. The crude yellow solid was stirred in water (100 mL) and was isolated by filtration, dried under vacuum, and recrystallized from 1,2-dichloroethane to yield 4-{[(3-nitroquinolin-4-yl)amino]methyl}tetrahydro-2H-pyran-4-ol as bright yellow crystals (15.6 g, 90%).

Workup

  1. customwas isolated by filtration
  2. customdried under vacuum
  3. customrecrystallized from 1,2-dichloroethane

Sources & evidence

ORD record
ord-44b0f603324644258a8f588b5d525c59
Source dataset
uspto-grants-2013_09
Patent number
US08541438B2

Linked notes

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