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

HRID 598008

반응식

HRID 598008 반응식
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

참가 물질

7

반응물 3

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

생성물 1

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

시약·촉매·용매 3

HCID 114742621,1'-Diethyl-4,4'-bipyridinium dibromide촉매HCID 962Water용매3회HCID 6344Dichloromethane용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-6766aafd70ff43cdb71f2c8366318d02
출처 데이터셋
uspto-grants-2011_03
특허 번호
US07897609B2

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