Triethylamine → 1-{[(3-Nitroquinolin-4-yl)amino]methyl}cyclopropanol

HRID 521333Notes

Reaction equation

HRID 521333 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:20])[CH2:19][CH2:18]1.C(N(CC)CC)C>ClCCl>[NH2:15][CH2:16][C:17]1([OH:20])[CH2:19][CH2:18]1.[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:20])[CH2:19][CH2:18]1)=[CH:10][CH:9]=[CH:8][CH:7]=2)([O-:14])=[O:13]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 112758084-Chloro-3-nitroquinolineHCID 126096231-(Aminomethyl)cyclopropan-1-ol

Product 2

HCID 126096231-(Aminomethyl)cyclopropan-1-olHCID 574554091-{[(3-Nitroquinolin-4-yl)amino]methyl}cyclopropanolYield 189%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

1-(Aminomethyl)cyclopropanol was prepared using the method of I. L. Lysenko and O. G. Kulinkovich, Russ. J. Org. Chem., 37, pp. 1238-1243 (2001). A solution of 4-chloro-3-nitroquinoline (7.28 g, 34.9 mmol) in dichloromethane (30 mL) was added dropwise to a 0° C. stirred suspension of 1-(aminomethyl)cyclopropanol (36.7 mmol) and triethylamine (6.30 mL, 45.4 mmol) in dichloromethane (120 mL). The mixture was stirred at room temperature for 3 days, then was concentrated under reduced pressure. The residue was suspended in water (150 mL) and was stirred for 3 hours. The solid was isolated by filtration, washed with water (50 mL), and dried in a vacuum oven at 75° C. to afford 8.99 g of 1-{[(3-nitroquinolin-4-yl)amino]methyl}cyclopropanol as a yellow solid.

Workup

  1. stirringThe mixture was stirred at room temperature for 3 days
  2. concentrationwas concentrated under reduced pressure
  3. stirringwas stirred for 3 hours
  4. customThe solid was isolated by filtration
  5. washwashed with water (50 mL)
  6. customdried in a vacuum oven at 75° C.

Sources & evidence

ORD record
ord-f2f7a024c7214080a46ad4a62f273265
Source dataset
uspto-grants-2016_05
Patent number
US09328110B2

Reaction notes

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