Triethylamine → 8-{[(3-Nitroquinolin-4-yl)amino]methyl}-1,4-dioxaspiro[4.5]decan-8-ol

HRID 44712

Reaction equation

HRID 44712 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].C(N(CC)CC)C.[NH2:22][CH2:23][C:24]1([OH:34])[CH2:33][CH2:32][C:27]2([O:31][CH2:30][CH2:29][O:28]2)[CH2:26][CH2:25]1>ClCCl.O>[N+:12]([C:3]1[CH:4]=[N:5][C:6]2[C:11]([C:2]=1[NH:22][CH2:23][C:24]1([OH:34])[CH2:33][CH2:32][C:27]3([O:31][CH2:30][CH2:29][O:28]3)[CH2:26][CH2:25]1)=[CH:10][CH:9]=[CH:8][CH:7]=2)([O-:14])=[O:13]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 112758084-Chloro-3-nitroquinolineHCID 434366478-(Aminomethyl)-1,4-dioxaspiro[4.5]decan-8-ol

Product 1

HCID 669191558-{[(3-Nitroquinolin-4-yl)amino]methyl}-1,4-dioxaspiro[4.5]decan-8-olYield 95.1%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

To a 0° C. solution of 4-chloro-3-nitroquinoline (7.50 g, 36.0 mmol) and triethylamine (7.5 mL, 54 mmol) in dichloromethane (150 mL) was added 8-(aminomethyl)-1,4-dioxaspiro[4.5]decan-8-ol (8.10 g, 43.1 mmol). The reaction was allowed to warm to rt and stir overnight, then was concentrated under reduced pressure to yield a yellow solid. The solid was stirred in water (500 mL) and was isolated by filtration, dried under vacuum, and recrystallized from toluene (280 mL) to yield 8-{[(3-nitroquinolin-4-yl)amino]methyl}-1,4-dioxaspiro[4.5]decan-8-ol as bright yellow crystals (12.3 g, 72%).

Workup

  1. concentrationwas concentrated under reduced pressure
  2. customto yield a yellow solid
  3. customwas isolated by filtration
  4. customdried under vacuum
  5. customrecrystallized from toluene (280 mL)

Sources & evidence

ORD record
ord-8f8cae2b9bf24dc79721f2f601b073df
Source dataset
uspto-grants-2013_09
Patent number
US08541438B2

Linked notes

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