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

HRID 598007Notes

Reaction equation

HRID 598007 reaction equation
C(N(CC)CC)C.[Br:8][C:9]1[CH:18]=[C:17]2[C:12]([C:13](Cl)=[C:14]([N+:19]([O-:21])=[O:20])[CH:15]=[N:16]2)=[N:11][CH:10]=1.[CH2:23]([NH2:27])[CH:24]([CH3:26])[CH3:25]>ClCCl>[Br:8][C:9]1[CH:18]=[C:17]2[C:12]([C:13]([NH:27][CH2:23][CH:24]([CH3:26])[CH3:25])=[C:14]([N+:19]([O-:21])=[O:20])[CH:15]=[N:16]2)=[N:11][CH:10]=1

Participants

5

Reactant 3

HCID 6558IsobutylamineHCID 8471TriethylamineHCID 574578377-Bromo-4-chloro-3-nitro[1,5]naphthyridine

Product 1

HCID 670522117-bromo-N-(2-methylpropyl)-3-nitro[1,5]naphthyridin-4-amineYield 98.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Triethylamine (17.97 mL, 129.0 mmol) was added to a solution of 7-bromo-4-chloro-3-nitro[1,5]naphthyridine (24.8 g, 86.0 mmol) in dichloromethane (200 mL) at 0° C. Isobutylamine (9.40 mL, 94.6 mmol) was added dropwise to the mixture, and the mixture was stirred for 3 hours at ambient temperature. The reaction mixture was condensed under reduced pressure to a solid, which was triturated with water (200 mL). The precipitate was filtered, washed sequentially with water and hexanes, and dried to yield 27.5 g of 7-bromo-3-nitro[1,5]naphthyridin-4-yl-(2-methylpropyl)amine as a yellow powder, mp 114-115° C.

Workup

  1. customcondensed under reduced pressure to a solid, which
  2. customwas triturated with water (200 mL)
  3. filtrationThe precipitate was filtered
  4. washwashed sequentially with water and hexanes
  5. customdried

Sources & evidence

ORD record
ord-06659af59b464135a880d92ff7aeb186
Source dataset
uspto-grants-2011_03
Patent number
US07897609B2

Reaction notes

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