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

HRID 598008

反応式

HRID 598008 の反応式
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

参加物

7

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 3

HCID 114742621,1'-Diethyl-4,4'-bipyridinium dibromide触媒HCID 962Water溶媒3 回HCID 6344Dichloromethane溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-6766aafd70ff43cdb71f2c8366318d02
出典データセット
uspto-grants-2011_03
特許番号
US07897609B2

関連ノート

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