Aluminium lithium hydride → HCID 22677536、化合物

HRID 378776

反応式

HRID 378776 の反応式
[H-].[Al+3].[Li+].[H-].[H-].[H-].[Br:7][C:8]1[N:13]=[C:12]([C:14]([O:16][CH3:17])=[O:15])[C:11]([Cl:18])=[C:10]([N+:19]([O-])=O)[CH:9]=1.O.[NH4+].[OH-]>O1CCCC1.[Ti](Cl)(Cl)(Cl)Cl>[NH2:19][C:10]1[CH:9]=[C:8]([Br:7])[N:13]=[C:12]([C:14]([O:16][CH3:17])=[O:15])[C:11]=1[Cl:18]

参加物

6

反応物 3

HCID 21226445Aluminium lithium hydrideHCID 21696610HCID 21696610、化合物HCID 86589665Water ammonium hydroxide

生成物 1

HCID 22677536HCID 22677536、化合物

試薬・触媒・溶媒 2

HCID 24193Titanium Tetrachloride触媒HCID 8028Tetrahydrofuran溶媒2 回

実験手順

To a solution of titanium tetrachloride (0.015 mol, 2.8 g) in tetrahydrofuran (50 mL) was added lithium aluminum hydride (0.0175 mol, 0.7 g). The black slurry was stirred 15 min before adding methyl 6-bromo-3-chloro-4-nitropyridine-2-carboxylate, N-oxide (0.007 mol, 2.3 g) in THF (25 mL). The solution was stirred 1 hr before pouring into 1:1 H2O/NH4OH and filtering. The filtrate was extracted with EtOAc (2×75 mL). The organic phase was dried (Na2SO4), and concentrated. The red solid was chromatographed over silica in 4:1 EtOAc/hexane to give methyl 4-amino-6-bromo-3-chloropyridine-2-carboxylate (0.003 mol, 0.8 g); mp 194-5° C. 1H NMR(CDCl3): δ 3.95 (3H, s), 5.3 (2H, bs), 6.9 (1H, s).

後処理

  1. stirringThe solution was stirred 1 hr
  2. filtrationfiltering
  3. extractionThe filtrate was extracted with EtOAc (2×75 mL)
  4. dry with materialThe organic phase was dried (Na2SO4)
  5. concentrationconcentrated
  6. customThe red solid was chromatographed over silica in 4:1 EtOAc/hexane

出典と根拠

ORDレコード
ord-7c6086651c14412d9ff26ab9dd4627c3
出典データセット
uspto-grants-2001_10
特許番号
US06297197B1

関連ノート

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