N-bromobutanimide → Ethyl 2-bromo-6-(1,1-dimethylethyl)-3-hydroxy-4-pyridinecarboxylate

HRID 735802ノート

反応式

HRID 735802 の反応式
[CH2:1]([O:3][C:4](=[O:16])[C:5]1[C:10]([OH:11])=[CH:9][N:8]=[C:7]([C:12]([CH3:15])([CH3:14])[CH3:13])[CH:6]=1)[CH3:2].[Br:17]N1C(=O)CCC1=O.C([O-])(O)=O.[Na+]>CN(C=O)C>[CH2:1]([O:3][C:4](=[O:16])[C:5]1[CH:6]=[C:7]([C:12]([CH3:15])([CH3:14])[CH3:13])[N:8]=[C:9]([Br:17])[C:10]=1[OH:11])[CH3:2]

参加物

5

反応物 3

HCID 67184N-bromobutanimideHCID 516892Sodium BicarbonateHCID 58980622HCID 58980622、化合物

生成物 1

HCID 58980648Ethyl 2-bromo-6-(1,1-dimethylethyl)-3-hydroxy-4-pyridinecarboxylate収率 96%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

To a solution of the above isonicotinic acid ethyl ester (2.0 g, 9.47 mmol) in DMF (20 mL) was added N-bromosuccinimide (1.85 g, 10.4 mmol). The solution was stirred at room temperature for 0.5 h then poured into saturated aqueous NaHCO3. The aqueous layer was extracted with diethyl ether and the combined organic layers were washed with saturated aqueous NaHCO3, dried over sodium sulfate, filtered, and concentrated in vacuo to provide 2-bromo-6-tert-butyl-3-hydroxy-isonicotinic acid ethyl ester (2.74 g, 96%) as a pale yellow oil which was utilized without further purification.

後処理

  1. extractionThe aqueous layer was extracted with diethyl ether
  2. washthe combined organic layers were washed with saturated aqueous NaHCO3
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo

出典と根拠

ORDレコード
ord-81c9bb463bae45d7a92fa3b1b3b274e9
出典データセット
uspto-grants-2009_09
特許番号
US07592332B2

反応ノート

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