Toluene → Ethyl 4-chloro-8-(trifluoromethyl)quinoline-3-carboxylate

HRID 2104474

反応式

HRID 2104474 の反応式
[CH2:1]([O:3][C:4]([C:6]1[CH:7]=[N:8][C:9]2[C:14]([C:15]=1O)=[CH:13][CH:12]=[CH:11][C:10]=2[C:17]([F:20])([F:19])[F:18])=[O:5])[CH3:2].C1(C)C=CC=CC=1.O=P(Cl)(Cl)[Cl:30].C([O-])(O)=O.[Na+]>C(OCC)(=O)C>[CH2:1]([O:3][C:4]([C:6]1[CH:7]=[N:8][C:9]2[C:14]([C:15]=1[Cl:30])=[CH:13][CH:12]=[CH:11][C:10]=2[C:17]([F:20])([F:19])[F:18])=[O:5])[CH3:2]

参加物

6

反応物 4

HCID 1140TolueneHCID 24813Phosphorus oxychlorideHCID 516892Sodium BicarbonateHCID 178469613HCID 178469613、化合物

生成物 1

HCID 725465Ethyl 4-chloro-8-(trifluoromethyl)quinoline-3-carboxylate

試薬・触媒・溶媒 1

HCID 8857Ethyl Acetate溶媒

実験手順

4-Hydroxy-8-(trifluoromethyl)-3-quinolinecarboxylic acid ethyl ester (compound of formula (V)), 11.27 g, 39.55 mmol) was taken into toluene (125 mL), then POCl3 (7.4 mL, 79.08 mmol) was added and the mixture was refluxed for 1.5 hours. The reaction was carefully poured into ice-water with vigorous stirring, then added carefully added saturated NaHCO3 until the solution was neutral. Dilute with ethyl acetate and separate the layers. The organic layer was dried over MgSO4, filtered and concentrated. The resulting material was passed through a short silica gel plug using 10% ethyl acetate in hexane. Concentration and drying under high vacuum yielded 9.93 g of the title compound as a white solid.

後処理

  1. temperaturethe mixture was refluxed for 1.5 hours
  2. customseparate the layers
  3. dry with materialThe organic layer was dried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. concentrationConcentration
  7. customdrying under high vacuum

出典と根拠

ORDレコード
ord-c5a3fd7dce1d4682a2bb4285cef7041c
出典データセット
uspto-grants-2009_08
特許番号
US07576215B2

関連ノート

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