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

HRID 547326Notes

Reaction equation

HRID 547326 reaction equation
[NH2:1][CH2:2][C:3]1([OH:6])[CH2:5][CH2:4]1.C(N(CC)CC)C.Cl[C:15]1[C:24]2[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=2)[N:18]=[CH:17][C:16]=1[N+:25]([O-:27])=[O:26]>ClCCl>[N+:25]([C:16]1[CH:17]=[N:18][C:19]2[C:24]([C:15]=1[NH:1][CH2:2][C:3]1([OH:6])[CH2:5][CH2:4]1)=[CH:23][CH:22]=[CH:21][CH:20]=2)([O-:27])=[O:26]

Participants

5

Reactant 3

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

Product 1

HCID 574554091-{[(3-Nitroquinolin-4-yl)amino]methyl}cyclopropanol

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a 0° C. mixture of 1-(aminomethyl)cyclopropanol (approximately 36.7 mmol, prepared as described by Lysenko, I. L. and Kulinkovich, O. G. Russ. i J. Org Chem. 2001, 17, 1238-1243) and triethylamine (6.30 mL, 45.4 mmol) in dichloromethane (120 mL) was added a solution of 4-chloro-3-nitroquinoline (7.28 g, 34.9 mmol) in dichloromethane (30 mL). The suspension was stirred at room temperature over the weekend. The dichloromethane was removed under reduced pressure and the residue was suspended in water (150 mL) and stirred at room temperature for 3 hours. A solid was isolated by filtration and dried in a vacuum oven to afford 8.99 g of 1-{[(3-nitroquinolin-4-yl)amino]methyl}cyclopropanol as a yellow solid.

Workup

  1. customprepared
  2. customThe dichloromethane was removed under reduced pressure
  3. stirringstirred at room temperature for 3 hours
  4. customA solid was isolated by filtration
  5. customdried in a vacuum oven

Sources & evidence

ORD record
ord-9ed1ea46ea094d319b414dea31d75cf2
Source dataset
uspto-grants-2011_05
Patent number
US07939526B2

Reaction notes

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