Hydrochloric Acid → Benzyl 6-(benzyloxy)quinoline-2-carboxylate

HRID 1497556ノート

反応式

HRID 1497556 の反応式
[OH:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[C:7]([C:12]([OH:14])=[O:13])[CH:6]=[CH:5]2.C(=O)([O-])[O-].[K+].[K+].[CH2:21](Br)[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1.Cl>CN(C)C=O.O1CCCC1.C(OCC)(=O)C>[CH2:21]([O:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[C:7]([C:12]([O:14][CH2:5][C:4]1[CH:9]=[CH:10][CH:11]=[CH:2][CH:3]=1)=[O:13])[CH:6]=[CH:5]2)[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1

参加物

8

反応物 4

HCID 313Hydrochloric AcidHCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 133367806-Hydroxyquinoline-2-carboxylic acid

生成物 1

HCID 90282113Benzyl 6-(benzyloxy)quinoline-2-carboxylate

試薬・触媒・溶媒 3

HCID 6228Dimethylformamide溶媒HCID 8028Tetrahydrofuran溶媒HCID 8857Ethyl Acetate溶媒

反応条件

温度
50 °C

実験手順

To a solution of 6-hydroxyquinoline-2-carboxylic acid (2.00 g) in N,N-dimethylformamide (20.0 mL) were added potassium carbonate (3.07 g) and benzyl bromide (3.02 mL), followed by stirring at 50° C. for 6 hours. The reaction mixture was left to be cooled, 1 M hydrochloric acid, ethyl acetate, and tetrahydrofuran were added thereto, and the organic layer was extracted. The organic layer was washed with water and a saturated aqueous sodium chloride solution, then dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The residue was purified by hexane-ethyl acetate to obtain benzyl 6-(benzyloxy)quinoline-2-carboxylate (1.80 g).

後処理

  1. waitThe reaction mixture was left
  2. temperatureto be cooled
  3. extractionthe organic layer was extracted
  4. washThe organic layer was washed with water
  5. dry with materiala saturated aqueous sodium chloride solution, then dried over anhydrous sodium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified by hexane-ethyl acetate

出典と根拠

ORDレコード
ord-b36b13778c40405584312bdbdbe848c2
出典データセット
uspto-grants-2015_12
特許番号
US09199927B2

反応ノート

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