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

HRID 547314Notes

Reaction equation

HRID 547314 reaction equation
[NH2:1][CH2:2][C:3]1([OH:7])[CH2:6][CH2:5][CH2:4]1.C(N(CC)CC)C.Cl[C:16]1[C:25]2[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=2)[N:19]=[CH:18][C:17]=1[N+:26]([O-:28])=[O:27]>ClCCl>[N+:26]([C:17]1[CH:18]=[N:19][C:20]2[C:25]([C:16]=1[NH:1][CH2:2][C:3]1([OH:7])[CH2:6][CH2:5][CH2:4]1)=[CH:24][CH:23]=[CH:22][CH:21]=2)([O-:28])=[O:27]

Participants

5

Reactant 3

HCID 8471Triethylamine2×HCID 112758084-Chloro-3-nitroquinolineHCID 282600091-(Aminomethyl)cyclobutan-1-ol

Product 1

HCID 574578111-{[(3-Nitroquinolin-4-yl)amino]methyl}cyclobutanolYield 75.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 1-(aminomethyl)cyclobutanol (62.5 mmol) in dichloromethane (312 mL) was added triethylamine (8.71 mL, 62.5 mmol) and 4-chloro-3-nitroquinoline (13.04 g, 62.5 mmol). More triethylamine (3 mL) was added almost immediately. The reaction was stirred under N2 for 10 days at room temperature, then was diluted with dichloromethane and washed with 1 M aqueous NaOH. A solid formed and was isolated by filtration. The organic layer was washed with water and brine, dried over Na2SO4, filtered, and concentrated under reduced pressure to yield a solid that was crystallized from 2-propanol. The resulting crystals were combined with the solid that was isolated from the extraction and the mixture was triturated with hot 2-propanol. The solid was isolated by filtration, washed with diethyl ether, and air dried to yield 12.83 g of 1-{[(3-nitroquinolin-4-yl)amino]methyl}cyclobutanol as yellow crystals.

Workup

  1. washwashed with 1 M aqueous NaOH
  2. customA solid formed
  3. customwas isolated by filtration
  4. washThe organic layer was washed with water and brine
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure
  8. customto yield a solid
  9. customthat was crystallized from 2-propanol
  10. customthat was isolated from the extraction
  11. customthe mixture was triturated with hot 2-propanol
  12. customThe solid was isolated by filtration
  13. washwashed with diethyl ether, and air
  14. customdried

Sources & evidence

ORD record
ord-0c9e4e45ec2b40b7bc33e7cec8a7bd85
Source dataset
uspto-grants-2011_05
Patent number
US07939526B2

Reaction notes

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