Benzyl Bromide → Methyl 1-benzyl-5-chloro-4-oxo-1,4-dihydrocinnoline-3-carboxylate

HRID 598155노트

반응식

HRID 598155 반응식
[Cl:1][C:2]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:3]=1[C:4](=[O:16])[C:5]([C:12]([O:14][CH3:15])=[O:13])=[N:6][NH:7]2.[CH2:17](Br)[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1.[H-].[Na+]>CN(C)C=O>[CH2:17]([N:7]1[C:8]2[C:3](=[C:2]([Cl:1])[CH:11]=[CH:10][CH:9]=2)[C:4](=[O:16])[C:5]([C:12]([O:14][CH3:15])=[O:13])=[N:6]1)[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1

참가 물질

5

반응물 3

HCID 7498Benzyl BromideHCID 24758Sodium hydrideHCID 67267740Methyl 5-chloro-4-oxo-1,4-dihydrocinnoline-3-carboxylate

생성물 1

HCID 67266995Methyl 1-benzyl-5-chloro-4-oxo-1,4-dihydrocinnoline-3-carboxylate수율 62.3%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

To 1.00 g (4.2 mmol) of methyl 5-chloro-4-oxo-1,4-dihydrocinnoline-3-carboxylate and 0.86 g (5.0 mmol) of benzyl bromide in 30 mL of dimethylformamide was added 0.20 g (5.0 mmol) of sodium hydride (60% dispersion in mineral oil). The mixture was stirred for 4 h at room temperature and quenched with water. The mixture was extracted with ethyl acetate and the combined organic layers were washed with brine, dried over sodium sulfate, filtered and concentrated onto silica gel. The crude material was purified by flash chromatography eluting with a 33-50% ethyl acetate/hexanes gradient mixture to give 0.86 g (62%) of the title compound as a light yellow solid.

후처리

  1. customquenched with water
  2. extractionThe mixture was extracted with ethyl acetate
  3. washthe combined organic layers were washed with brine
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated onto silica gel
  7. customThe crude material was purified by flash chromatography
  8. washeluting with a 33-50% ethyl acetate/hexanes gradient mixture

출처 및 근거

ORD 기록
ord-1525a56fbebb42908cffa07d39781943
출처 데이터셋
uspto-grants-2011_03
특허 번호
US07897607B2

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