Hydrochloric Acid → 1-(6-Bromo-pyridin-2-ylmethyl)-4-oxo-1,4-dihydro-quinoline-3-carboxylic acid

HRID 227025ノート

反応式

HRID 227025 の反応式
C([O:3][C:4]([C:6]1[C:15](=[O:16])[C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[N:8]([CH2:17][C:18]2[CH:23]=[CH:22][CH:21]=[C:20]([Br:24])[N:19]=2)[CH:7]=1)=[O:5])C.[OH-].[Li+].CO.Cl>CO.O>[Br:24][C:20]1[N:19]=[C:18]([CH2:17][N:8]2[C:9]3[C:14](=[CH:13][CH:12]=[CH:11][CH:10]=3)[C:15](=[O:16])[C:6]([C:4]([OH:5])=[O:3])=[CH:7]2)[CH:23]=[CH:22][CH:21]=1

参加物

6

反応物 4

HCID 313Hydrochloric AcidHCID 887MethanolHCID 3939Lithium HydroxideHCID 577546321-(6-Bromo-pyridin-2-ylmethyl)-4-oxo-1,4-dihydro-quinoline-3-carboxylic acid ethyl ester

生成物 1

HCID 577547691-(6-Bromo-pyridin-2-ylmethyl)-4-oxo-1,4-dihydro-quinoline-3-carboxylic acid収率 68.7%

試薬・触媒・溶媒 1

HCID 22242641Methanol--water (1/1)溶媒

反応条件

温度
65 °C

実験手順

14.9 g (38.5 mmol) of 1-(6-bromo-pyridin-2-ylmethyl)-4-oxo-1,4-dihydro-quinoline-3-carboxylic acid ethyl ester was dissolved/suspended in 300 mL of a 1:1 methanol-water mixture. 1.11 g (46.2 mmol) of lithium hydroxide was added and the mixture was heated up to 65° C. and stirred overnight. The mixture was cooled down to r.t., 300 mL of methanol and 4 mL of concentrated aqueous HCl were added and the solids were filtered off. The solids were then dissolved/suspended in 300 mL ethanol, brought to reflux, cooled down to rt, filtered, washed with 50 mL diethyl ether and dried to yield 9.5 g of the product as a white solid.

後処理

  1. temperatureThe mixture was cooled down to r.t.
  2. filtrationthe solids were filtered off
  3. temperatureto reflux
  4. temperaturecooled down to rt
  5. filtrationfiltered
  6. washwashed with 50 mL diethyl ether
  7. customdried

出典と根拠

ORDレコード
ord-eac20ea6798b4b23a6aae33fc8a8d005
出典データセット
uspto-grants-2009_07
特許番号
US07557213B2

反応ノート

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