Pyridine → 6-Hydroxy-2-oxo-1,2-dihydroquinoline-5-carbaldehyde

HRID 579469

반응식

HRID 579469 반응식
BrC1C(=O)[O:4][C:5]2[C:10](C=1C)=[CH:9]C=[C:7]([OH:13])[CH:6]=2.[N:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.[O:21](C(C(F)(F)F)=O)C(C(F)(F)F)=O>C(Cl)Cl>[OH:4][C:5]1[CH:10]=[CH:9][C:20]2[NH:15][C:16](=[O:21])[CH:17]=[CH:18][C:19]=2[C:6]=1[CH:7]=[O:13]

참가 물질

5

반응물 3

HCID 1049PyridineHCID 9845Trifluoroacetic anhydrideHCID 53375453-Bromo-7-hydroxy-4-methylchromen-2-one

생성물 1

HCID 866834296-Hydroxy-2-oxo-1,2-dihydroquinoline-5-carbaldehyde수율 95.3%

시약·촉매·용매 1

HCID 6344Dichloromethane용매2회

실험 절차

Compound 1 (38 g, 249.6 mmol) and pyridine (21.7 g, 275.0 mmol) were dissolved in DCM (750 mL). (CF3CO)2O (57.7 g, 275.0 mmol) was added dropwise at 0° C. After that the reaction mixture was stirred at RT for 16 h. The reaction mixture was diluted with DCM (500 mL), washed with 1N HCl, concentrated. The residue was purified by silica gel column (PE:EA=10:1), afforded compound 2 (45 g, 72%) as white solid.

후처리

  1. washwashed with 1N HCl
  2. concentrationconcentrated
  3. customThe residue was purified by silica gel column (PE:EA=10:1)

출처 및 근거

ORD 기록
ord-e66b7c0178974a83b40a588fcf4809cb
출처 데이터셋
uspto-grants-2015_05
특허 번호
US09040714B2

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