Potassium Carbonate → 7-bromo-N4-(2-methylpropyl)[1,5]naphthyridine-3,4-diamine

HRID 598008

Reaction equation

HRID 598008 reaction equation
S(S([O-])=O)([O-])=O.[Na+].[Na+].C(=O)([O-])[O-].[K+].[K+].[Br:15][C:16]1[CH:25]=[C:24]2[C:19]([C:20]([NH:29][CH2:30][CH:31]([CH3:33])[CH3:32])=[C:21]([N+:26]([O-])=O)[CH:22]=[N:23]2)=[N:18][CH:17]=1>O.ClCCl.CC[N+]1C=CC(C2C=C[N+](CC)=CC=2)=CC=1.[Br-].[Br-]>[Br:15][C:16]1[CH:25]=[C:24]2[C:19]([C:20]([NH:29][CH2:30][CH:31]([CH3:33])[CH3:32])=[C:21]([NH2:26])[CH:22]=[N:23]2)=[N:18][CH:17]=1

Participants

7

Reactant 3

HCID 11430Potassium CarbonateHCID 24489Sodium DithioniteHCID 670522117-bromo-N-(2-methylpropyl)-3-nitro[1,5]naphthyridin-4-amine

Product 1

HCID 688188847-bromo-N4-(2-methylpropyl)[1,5]naphthyridine-3,4-diamineYield 89.3%

Reagents, catalysts & solvents 3

HCID 114742621,1'-Diethyl-4,4'-bipyridinium dibromideCatalystHCID 962WaterSolvent3×HCID 6344DichloromethaneSolvent

Procedure

A solution of sodium dithionite (77.95 g, 380.6 mmol) and potassium carbonate (58.35 g, 422.2 mmol) in water (250 mL) was added dropwise to a mechanically stirred solution of 7-bromo-3-nitro[1,5]naphthyridin-4-yl-(2-methylpropyl)amine (27.6 g, 84.6 mmol) and ethyl viologen dibromide (0.63 g, 1.7 mmol) in dichloromethane (300 mL) and water (50 mL). The reaction mixture was stirred overnight at ambient temperature. Water (500 mL) was added, and the reaction mixture was stirred for 10 minutes. The organic layer was separated and the aqueous layer was filtered through WHATMAN paper to remove insoluble material. The emulsion-free filtrate was extracted with dichloromethane, washed sequentially with water and brine, dried over sodium sulfate, filtered, and concentrated under reduced pressure to yield 22.3 g of 7-bromo-N4-(2-methylpropyl)[1,5]naphthyridine-3,4-diamine as an orange solid.

Workup

  1. stirringthe reaction mixture was stirred for 10 minutes
  2. customThe organic layer was separated
  3. filtrationthe aqueous layer was filtered through WHATMAN paper
  4. customto remove insoluble material
  5. extractionThe emulsion-free filtrate was extracted with dichloromethane
  6. washwashed sequentially with water and brine
  7. dry with materialdried over sodium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-6766aafd70ff43cdb71f2c8366318d02
Source dataset
uspto-grants-2011_03
Patent number
US07897609B2

Linked notes

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