Triethylamine → 4-[(3-Nitroquinolin-4-yl)amino]butan-1-ol

HRID 2404990Notes

Reaction equation

HRID 2404990 reaction equation
C(N(CC)CC)C.Cl[C:9]1[C:18]2[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=2)[N:12]=[CH:11][C:10]=1[N+:19]([O-:21])=[O:20].[NH2:22][CH2:23][CH2:24][CH2:25][CH2:26][OH:27]>ClCCl>[N+:19]([C:10]1[CH:11]=[N:12][C:13]2[C:18]([C:9]=1[NH:22][CH2:23][CH2:24][CH2:25][CH2:26][OH:27])=[CH:17][CH:16]=[CH:15][CH:14]=2)([O-:21])=[O:20]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 258684-Amino-1-butanolHCID 112758084-Chloro-3-nitroquinoline

Product 1

HCID 121061814-[(3-Nitroquinolin-4-yl)amino]butan-1-olYield 193%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Triethylamine (11.8 g, 1.1 eq.) was added to a suspension of 4-chloro-3-nitroquinoline (20 g, 48 mmol. 1.0 eq.) in dichloromethane (200 mL). A solution of 4-aminobutan-1-ol (9.6 g, 1.1 eq.) in dichloromethane (50 mL) was added dropwise. The reaction mixture was stirred for 2 hours and then concentrated under reduced pressure. The residue was triturated with water. The resulting solid was isolated by filtration, air dried, and purified by chromatography (silica gel eluting sequentially with dichloromethane and 5/95 methanol/dichloromethane) to provide 24.2 g of 4-[(3-nitroquinolin-4-yl)amino]butan-1-ol.

Workup

  1. concentrationconcentrated under reduced pressure
  2. customThe residue was triturated with water
  3. customThe resulting solid was isolated by filtration, air
  4. customdried
  5. custompurified by chromatography (silica gel eluting sequentially with dichloromethane and 5/95 methanol/dichloromethane)

Sources & evidence

ORD record
ord-d00f5b040e2042c6ac7e7dea572b20bf
Source dataset
uspto-grants-2014_08
Patent number
US08802853B2

Reaction notes

Loading…