Sodium hydride → 5-Chloro-1-(4-methoxy-benzyl)-3-nitro-1H-pyridin-2-one

HRID 1478243ノート

反応式

HRID 1478243 の反応式
[Cl:1][C:2]1[CH:3]=[C:4]([N+:9]([O-:11])=[O:10])[C:5]([OH:8])=[N:6][CH:7]=1.[H-].[Na+].[CH3:14][O:15][C:16]1[CH:23]=[CH:22][C:19]([CH2:20]Cl)=[CH:18][CH:17]=1>CN(C=O)C>[Cl:1][C:2]1[CH:3]=[C:4]([N+:9]([O-:11])=[O:10])[C:5](=[O:8])[N:6]([CH2:20][C:19]2[CH:22]=[CH:23][C:16]([O:15][CH3:14])=[CH:17][CH:18]=2)[CH:7]=1

参加物

5

反応物 3

HCID 24758Sodium hydrideHCID 699934-Methyloxybenzyl chlorideHCID 178526657HCID 178526657、化合物

生成物 1

HCID 896013295-Chloro-1-(4-methoxy-benzyl)-3-nitro-1H-pyridin-2-one収率 58.4%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
80 °C

実験手順

To a stirred solution of 5-chloro-3-nitropyridin-2-ol (12 g, 68.8 mmol) in DMF (80 ml) was added in several portions NaH (3.30 g, 83 mmol) at 0° C. The reaction mixture was stirred in the ice-bath for 2 hours. Then 4-methoxybenzyl chloride (11.19 ml, 83 mmol) was added and the reaction mixture was heated at 80° C. for 1 hour. The reaction mixture was quenched with aqueous saturated NaHCO3 solution and extracted twice with EtOAc. The organic layers were washed with brine, combined, dried over sodium sulphate, filtered and evaporated. The crude material was taken up in n-heptane/AcOEt 10:1 and the suspension was kept in the sonic bath for 10 minutes. After filtration the filtrate was washed with n-heptane and dried in vacuum to obtain 11.84 g (40.2 mmol, 58.4% yield) of the title compound as a greenish solid. LCMS: (M+H)=295; tR=0.94 min (LC-MS 4). 1H-NMR (d6-DMSO, 400 MHz) 8.72 (d, 1H) 8.56 (d, 1H) 7.36 (d, 2H) 6.94 (d, 2H) 5.13 (s, 2H) 3.74 (s, 3H).

後処理

  1. customThe reaction mixture was quenched with aqueous saturated NaHCO3 solution
  2. extractionextracted twice with EtOAc
  3. washThe organic layers were washed with brine
  4. dry with materialdried over sodium sulphate
  5. filtrationfiltered
  6. customevaporated
  7. filtrationAfter filtration the filtrate
  8. washwas washed with n-heptane
  9. customdried in vacuum

出典と根拠

ORDレコード
ord-5abc34129d91467492daad6f06dec904
出典データセット
uspto-grants-2016_08
特許番号
US09403827B2

反応ノート

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