Aluminium lithium hydride → HCID 22677536, 화합물

HRID 378776

반응식

HRID 378776 반응식
[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]

참가 물질

6

반응물 3

HCID 21226445Aluminium lithium hydrideHCID 21696610HCID 21696610, 화합물HCID 86589665Water ammonium hydroxide

생성물 1

HCID 22677536HCID 22677536, 화합물

시약·촉매·용매 2

HCID 24193Titanium Tetrachloride촉매HCID 8028Tetrahydrofuran용매2회

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-7c6086651c14412d9ff26ab9dd4627c3
출처 데이터셋
uspto-grants-2001_10
특허 번호
US06297197B1

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