Phosphorus oxychloride → 4-Chloro-7-fluoro-6-methoxy-3-quinolinecarbonitrile

HRID 1837330ノート

反応式

HRID 1837330 の反応式
[F:1][C:2]1[CH:11]=[C:10]2[C:5]([C:6](=O)[C:7]([C:12]#[N:13])=[CH:8][NH:9]2)=[CH:4][C:3]=1[O:15][CH3:16].P(Cl)(Cl)([Cl:19])=O>>[Cl:19][C:6]1[C:5]2[C:10](=[CH:11][C:2]([F:1])=[C:3]([O:15][CH3:16])[CH:4]=2)[N:9]=[CH:8][C:7]=1[C:12]#[N:13]

参加物

3

反応物 2

HCID 24813Phosphorus oxychlorideHCID 121507027-FLUORO-6-METHOXY-4-OXO-1,4-DIHYDROQUINOLINE-3-CARBONITRILE

生成物 1

HCID 121507034-Chloro-7-fluoro-6-methoxy-3-quinolinecarbonitrile収率 58.1%

実験手順

A mixture of 7-fluoro-6-methoxy-4-oxo-1,4-dihydro-3-quinolinecarbonitrile (1.0 g, 4.59 mmol) and 14 g of phosphorous oxychloride is heated at reflux for 30 minutes then concentrated in vacuo. The residue is partitioned between aqueous sodium bicarbonate and ethyl acetate. The organic layer is dried over magnesium sulfate, filtered and concentrated on to silica gel. Purification by flash column chromatography eluting with a gradient of 1:5 ethyl acetate:hexane to 1:1 ethyl acetate:hexane, provides 631 mg of 4-chloro-7-fluoro-6-methoxy-3-quinolinecarbonitrile, mp 160-162° C.

後処理

  1. temperatureis heated
  2. temperatureat reflux for 30 minutes
  3. concentrationthen concentrated in vacuo
  4. customThe residue is partitioned between aqueous sodium bicarbonate and ethyl acetate
  5. dry with materialThe organic layer is dried over magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated on to silica gel
  8. customPurification by flash column chromatography
  9. washeluting with a gradient of 1:5 ethyl acetate

出典と根拠

ORDレコード
ord-1d773e79593c4038aa9ab701fe56b3d3
出典データセット
uspto-grants-2004_08
特許番号
US06780996B2

反応ノート

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