Triethylamine → 3-[(3-Nitro[1,5]naphthyridin-4-yl)amino]propan-1-ol

HRID 1992589Notes

Reaction equation

HRID 1992589 reaction equation
Cl[C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][N:10]=2)[N:5]=[CH:4][C:3]=1[N+:12]([O-:14])=[O:13].C(N(CC)CC)C.[NH2:22][CH:23](C)[CH2:24][CH2:25][OH:26]>ClCCl.O>[N+:12]([C:3]1[CH:4]=[N:5][C:6]2[C:11]([C:2]=1[NH:22][CH2:23][CH2:24][CH2:25][OH:26])=[N:10][CH:9]=[CH:8][CH:7]=2)([O-:14])=[O:13]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 122027913-Aminobutan-1-olHCID 131227874-Chloro-3-nitro-1,5-naphthyridine

Product 1

HCID 685404393-[(3-Nitro[1,5]naphthyridin-4-yl)amino]propan-1-olYield 98%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of 4-chloro-3-nitro[1,5]naphthyridine (18.0 g, 85.9 mmol) in dichloromethane (220 mL) at room temperature was added triethylamine (15.6 mL, 112 mmol) and 3-amino-1-butanol (7.20 mL, 94.5 mmol). The solution was stirred for 4 hours and then was concentrated under reduced pressure to yield an orange solid. The solid was slurried in water (250 mL) for 30 minutes, isolated by filtration, washed with water (3×30 mL), and dried at 70° C. in a vacuum oven to afford 20.9 g of 3-[(3-nitro[1,5]naphthyridin-4-yl)amino]propan-1-ol as a yellow solid.

Workup

  1. concentrationwas concentrated under reduced pressure
  2. customto yield an orange solid
  3. customisolated by filtration
  4. washwashed with water (3×30 mL)
  5. customdried at 70° C. in a vacuum oven

Sources & evidence

ORD record
ord-a9f6cb9789d0424e8d656d863c1b4f5a
Source dataset
uspto-grants-2010_01
Patent number
US07648997B2

Reaction notes

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