Hydrochloric Acid → (E)-3-[2-cyclopropyl-4-(4-fluoro-phenyl)-quinolin-3-yl]-acrylic acid

HRID 1072287ノート

反応式

HRID 1072287 の反応式
[CH:1]1([C:4]2[C:13](/[CH:14]=[CH:15]/[CH:16]=[O:17])=[C:12]([C:18]3[CH:23]=[CH:22][C:21]([F:24])=[CH:20][CH:19]=3)[C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[N:5]=2)[CH2:3][CH2:2]1.P([O-])(O)(O)=[O:26].[Na+].OO.Cl([O-])=O.[Na+].O.O.O.O.O.S([O-])([O-])(=O)=S.[Na+].[Na+].Cl>C(#N)C.O>[CH:1]1([C:4]2[C:13](/[CH:14]=[CH:15]/[C:16]([OH:26])=[O:17])=[C:12]([C:18]3[CH:19]=[CH:20][C:21]([F:24])=[CH:22][CH:23]=3)[C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[N:5]=2)[CH2:3][CH2:2]1

参加物

9

反応物 6

HCID 313Hydrochloric AcidHCID 784Hydrogen PeroxideHCID 61475Sodium Thiosulfate PentahydrateHCID 9797032(E)-3-(2-Cyclopropyl-4-(4-fluorophenyl)quinolin-3-yl)acrylaldehydeHCID 23668197Sodium ChloriteHCID 23672064Monosodium phosphate

生成物 1

HCID 22392019(E)-3-[2-cyclopropyl-4-(4-fluoro-phenyl)-quinolin-3-yl]-acrylic acid

試薬・触媒・溶媒 2

HCID 962Water溶媒2 回HCID 6342Acetonitrile溶媒

実験手順

To a mixture of (E)-3-[2-Cyclopropyl-4-(4-fluoro-phenyl)-quinolin-3-yl]-propenal (50.0 g, 157.5 mmol) in acetonitrile (650 ml) and sodium dihydrogenphosphate (30.5 g, 220.5 mmol) in water (100 ml) is added hydrogen peroxide (18.8 g, 165.4 mmol) and a solution of sodium chlorite (25.0 g, 220.5 mmol) in water (120 ml) at 0° C. The reaction mixture is stirred in an ice bath for 120 min. Sodium thiosulfate pentahydrate (2.5 g, 10 mmol) and then 2M hydrochloric acid is added to adjust the pH to 2-3. After dilution with ethyl acetate (200 ml), the organic phase is separated and the pH of the aq. phase adjusted to 3-4 by addition of 2M sodium hydroxide. The reaction mixture is partitioned between ethyl acetate and water. The organic phases are separated, dried over magnesium sulphate and evaporated to afford (E)-3-[2-cyclopropyl-4-(4-fluoro-phenyl)-quinolin-3-yl]-acrylic acid. MS (ES): [M−H]− 332, Mp. 173-174° C.

後処理

  1. customat 0° C
  2. customAfter dilution with ethyl acetate (200 ml), the organic phase is separated
  3. additionthe pH of the aq. phase adjusted to 3-4 by addition of 2M sodium hydroxide
  4. customThe reaction mixture is partitioned between ethyl acetate and water
  5. customThe organic phases are separated
  6. dry with materialdried over magnesium sulphate
  7. customevaporated

出典と根拠

ORDレコード
ord-1cdf0c82b59c4209b0a508c03b4598df
出典データセット
uspto-grants-2005_06
特許番号
US06909003B2

反応ノート

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