Piconol → HCID 18357727, 화합물

HRID 427733노트

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HRID 427733 반응식
[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[CH2:7][OH:8].[H-].[Na+].Cl[C:12]1[C:17]([CH3:18])=[CH:16][C:15]([N+:19]([O-:21])=[O:20])=[CH:14][N:13]=1>CN(C)C=O>[CH3:18][C:17]1[C:12]([O:8][CH2:7][C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][N:1]=2)=[N:13][CH:14]=[C:15]([N+:19]([O-:21])=[O:20])[CH:16]=1

참가 물질

5

반응물 3

HCID 11474PiconolHCID 24758Sodium hydrideHCID 896482-Chloro-3-methyl-5-nitropyridine

생성물 1

HCID 18357727HCID 18357727, 화합물수율 51%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매2회

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온도
-20 °C

실험 절차

2-Pyridylcarbinol (1.96 g, 18 mmol) in dry dimethylformamide (20 ml) was cooled to −20° C. and treated with sodium hydride (0.48 g of 80% dispersion in mineral oil, 16 mmol). The mixture was stirred under argon at −20° C. for one hour then a solution of 2-chloro-3-methyl-5-nitropyridine (2.07 g, 12 mmol) in dry dimethylformamide (10 ml) was added and the mixture was allowed to warn to room temperature over 16 hours. The solvent was removed in vacuo and the residue partitioned between dichloromethane (3×100 ml) and 10% aqueous sodium hydroxide solution(75 ml). The combined organics were dried (Na2SO4) and evaporated in vacuo to a residue which was subjected to flash column chromatography with 1:1 ethyl acetate/petroleum ether as eluant to afford the title compound (1.47 g, 51%) as lemon yellow crystals.

후처리

  1. waitto warn to room temperature over 16 hours
  2. customThe solvent was removed in vacuo
  3. customthe residue partitioned between dichloromethane (3×100 ml) and 10% aqueous sodium hydroxide solution(75 ml)
  4. dry with materialThe combined organics were dried (Na2SO4)
  5. customevaporated in vacuo to a residue which

출처 및 근거

ORD 기록
ord-1bb25614cbb04cd19954d7e973d0c41c
출처 데이터셋
uspto-grants-2001_11
특허 번호
US06313145B1

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