Water → N-(2-Methylpropyl)-3-nitro-1,5-naphthyridin-4-amine

HRID 1907964Notes

Reaction equation

HRID 1907964 reaction equation
[CH2:1]([NH2:5])[CH:2]([CH3:4])[CH3:3].Cl[C:7]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][N:15]=2)[N:10]=[CH:9][C:8]=1[N+:17]([O-:19])=[O:18].O>ClCCl>[CH3:3][CH:2]([CH3:4])[CH2:1][NH:5][C:7]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][N:15]=2)[N:10]=[CH:9][C:8]=1[N+:17]([O-:19])=[O:18]

Participants

5

Reactant 3

HCID 962WaterHCID 6558IsobutylamineHCID 131227874-Chloro-3-nitro-1,5-naphthyridine

Product 1

HCID 54184816N-(2-Methylpropyl)-3-nitro-1,5-naphthyridin-4-amineYield 97.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Isobutylamine (15.6 mL, 157 mmol) was added dropwise to a 5° C. solution of 4-chloro-3-nitro[1,5]naphthyridine (15.0 g, 71.6 mmol) in dichloromethane (300 mL). The reaction was allowed to stir at room temperature for 4 hours, then was concentrated under reduced pressure to afford a residue that was treated with water (300 mL). The mixture was stirred for 30 minutes, then a solid was isolated by filtration, rinsed with water (100 mL), and dried in a vacuum oven at 50° C. overnight to afford 17.25 g of N-(2-methylpropyl)-3-nitro[1,5]naphthyridin-4-amine as a yellow solid.

Workup

  1. concentrationwas concentrated under reduced pressure
  2. customto afford a residue that
  3. stirringThe mixture was stirred for 30 minutes
  4. customa solid was isolated by filtration
  5. washrinsed with water (100 mL)
  6. customdried in a vacuum oven at 50° C. overnight

Sources & evidence

ORD record
ord-e89822c7b9534dccb7ec89e16f5931bc
Source dataset
uspto-grants-2013_12
Patent number
US08598192B2

Reaction notes

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