Hydrochloric Acid → 3-(4-Carboxybenzyl)-7-chloro-4-oxo-1-phenyl-1,4-dihydroquinoline-2-carboxylic acid methyl ester

HRID 1261756노트

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HRID 1261756 반응식
[CH3:1][O:2][C:3]([C:5]1[N:6]([C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)[C:7]2[C:12]([C:13](=[O:26])[C:14]=1[CH2:15][C:16]1[CH:21]=[CH:20][C:19]([C:22]([O:24]C)=[O:23])=[CH:18][CH:17]=1)=[CH:11][CH:10]=[C:9]([Cl:27])[CH:8]=2)=[O:4].[OH-].[Li+].Cl.C(OC)(=O)C>O1CCOCC1.O>[CH3:1][O:2][C:3]([C:5]1[N:6]([C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)[C:7]2[C:12]([C:13](=[O:26])[C:14]=1[CH2:15][C:16]1[CH:21]=[CH:20][C:19]([C:22]([OH:24])=[O:23])=[CH:18][CH:17]=1)=[CH:11][CH:10]=[C:9]([Cl:27])[CH:8]=2)=[O:4]

참가 물질

7

반응물 4

HCID 313Hydrochloric AcidHCID 3939Lithium Hydroxide2회HCID 6584Methyl AcetateHCID 598461727-Chloro-3-(4-methoxycarbonyl-benzyl)-4-oxo-1-phenyl-1,4-dihydro-quinoline-2-carboxylic acid methyl ester

생성물 1

HCID 251817183-(4-Carboxybenzyl)-7-chloro-4-oxo-1-phenyl-1,4-dihydroquinoline-2-carboxylic acid methyl ester수율 83.4%

시약·촉매·용매 2

HCID 962Water용매HCID 312751,4-Dioxane용매2회

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온도
25 °C

실험 절차

A 2 L three necked round bottom flask equipped with a mechanical stirrer, a nitrogen bubbler and a thermometer was charged with 7-chloro-3-(4-methoxycarbonyl-benzyl)-4-oxo-1-phenyl-1,4-dihydro-quinoline-2-carboxylic acid methyl ester (34 g, 73.6 mmol) methanol (600 mL) and 1,4-dioxane (300 mL). The resulting mixture was treated with lithium hydroxide (3.52 g, 146 mmol). The reaction was stirred at 25° C. over the weekend. At this time, the reaction was warmed to 35° C. and was stirred at 35° C. overnight. The reaction was then treated with additional lithium hydroxide (3.5 g, 1.46 mmol) and water (10 mL) and continued to stir at 35° C. overnight. At this time, additional 1,4-dioxane (300 mL) was added to the reaction. The reaction was stirred at 35° C. overnight. The reaction was then warmed to 40° C. where it stirred for 8 h and then was stirred at 35° C. overnight. At this time, the reaction was cooled to 25° C., treated with concentrated hydrochloric acid (25 mL) and methyl acetate (500 mL) and concentrated in vacuo. The resulting solids were collected by filtration, washed with methanol and dried in vacuo to afford 3-(4-carboxy-benzyl)-7-chloro-4-oxo-1-phenyl-1,4-dihydro-quinoline-2-carboxylic acid methyl ester (27.5 g). An additional amount of 3-(4-carboxy-benzyl)-7-chloro-4-oxo-1-phenyl-1,4-dihydro-quinoline-2-carboxylic acid methyl ester (3 g, total yield: 92.5%) was obtained through concentration of the filtrate and collection of the resulting solids. This material was used without further purification.

후처리

  1. temperatureAt this time, the reaction was warmed to 35° C.
  2. stirringwas stirred at 35° C. overnight
  3. stirringto stir at 35° C. overnight
  4. stirringThe reaction was stirred at 35° C. overnight
  5. temperatureThe reaction was then warmed to 40° C. where it
  6. stirringstirred for 8 h
  7. stirringwas stirred at 35° C. overnight
  8. temperatureAt this time, the reaction was cooled to 25° C.
  9. concentrationconcentrated in vacuo
  10. filtrationThe resulting solids were collected by filtration
  11. washwashed with methanol
  12. customdried in vacuo

출처 및 근거

ORD 기록
ord-2a71372f2fdb421ebc9ae2df7c1135a1
출처 데이터셋
uspto-grants-2013_06
특허 번호
US08471027B2

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