Isobutylamine → 7-bromo-N-(2-methylpropyl)-3-nitro[1,5]naphthyridin-4-amine

HRID 599439Notes

Reaction equation

HRID 599439 reaction equation
[CH2:1]([NH2:5])[CH:2]([CH3:4])[CH3:3].[Br:6][C:7]1[CH:16]=[C:15]2[C:10]([C:11](Cl)=[C:12]([N+:17]([O-:19])=[O:18])[CH:13]=[N:14]2)=[N:9][CH:8]=1>ClCCl>[Br:6][C:7]1[CH:16]=[C:15]2[C:10]([C:11]([NH:5][CH2:1][CH:2]([CH3:4])[CH3:3])=[C:12]([N+:17]([O-:19])=[O:18])[CH:13]=[N:14]2)=[N:9][CH:8]=1

Participants

4

Reactant 2

HCID 6558IsobutylamineHCID 574578377-Bromo-4-chloro-3-nitro[1,5]naphthyridine

Product 1

HCID 670522117-bromo-N-(2-methylpropyl)-3-nitro[1,5]naphthyridin-4-amineYield 95.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Isobutylamine (16.2 mL, 163 mmol) was added dropwise to a 0° C. solution of 7-bromo-4-chloro-3-nitro[1,5]naphthyridine (approximately 74.1 mmol) in dichloromethane (350 mL). The reaction mixture was allowed to stir and warm to room temperature for 3 hours, then was diluted with dichloromethane (50 mL) and washed with saturated aqueous sodium bicarbonate (300 mL). The aqueous layer was back-extracted with dichloromethane (2×75 mL). The organic layers were combined, dried over magnesium sulfate, filtered, and concentrated to afford 23.06 g of 7-bromo-N-(2-methylpropyl)-3-nitro[1,5]naphthyridin-4-amine as a yellow solid.

Workup

  1. washwashed with saturated aqueous sodium bicarbonate (300 mL)
  2. extractionThe aqueous layer was back-extracted with dichloromethane (2×75 mL)
  3. dry with materialdried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-6f081ad01ead46a9a4d0912290cc93ba
Source dataset
uspto-grants-2011_03
Patent number
US07897767B2

Reaction notes

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