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

HRID 1187396Notes

Reaction equation

HRID 1187396 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][CH2:23][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 90863-Amino-1-propanolHCID 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-propanol (7.20 ML, 94.5 mmol). The solution was stirred for 4 hours, 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-a0420650138b4db097a677f9aa851a31
Source dataset
uspto-grants-2014_03
Patent number
US08673932B2

Reaction notes

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