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

HRID 598155ノート

反応式

HRID 598155 の反応式
[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

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-1525a56fbebb42908cffa07d39781943
出典データセット
uspto-grants-2011_03
特許番号
US07897607B2

反応ノート

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