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

HRID 1181929노트

반응식

HRID 1181929 반응식
[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]

참가 물질

5

반응물 3

HCID 67184N-bromobutanimideHCID 516892Sodium BicarbonateHCID 58980622HCID 58980622, 화합물

생성물 1

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

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-bf7a752252b14877bfe2c52f9370fa9c
출처 데이터셋
uspto-grants-2007_10
특허 번호
US07285545B2

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