1,4-Dioxane → (S,E)-N-(a-ethylbenzyl)-3-[2-(3-carboxypropenoyl)aminoethoxy]-2-phenylquinoline-4-carboxamide

HRID 651068Notes

Reaction equation

HRID 651068 reaction equation
[CH2:1]([C@H:3]([NH:10][C:11]([C:13]1[C:22]2[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=2)[N:16]=[C:15]([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[C:14]=1[O:29][CH2:30][CH2:31][NH:32][C:33](=[O:40])/[CH:34]=[CH:35]/[C:36]([O:38]C)=[O:37])=[O:12])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1)[CH3:2].O1CCOCC1>[OH-].[Na+]>[CH2:1]([C@H:3]([NH:10][C:11]([C:13]1[C:22]2[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=2)[N:16]=[C:15]([C:23]2[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=2)[C:14]=1[O:29][CH2:30][CH2:31][NH:32][C:33](=[O:40])/[CH:34]=[CH:35]/[C:36]([OH:38])=[O:37])=[O:12])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1)[CH3:2]

Participants

4

Reactant 2

HCID 312751,4-DioxaneHCID 70250562(S,E)-N-(a-ethylbenzyl)-3-[2-(3-methoxycarbonylpropenoyl)aminoethoxy]-2-phenylquinoline-4-carboxamide2×

Product 1

HCID 70250619(S,E)-N-(a-ethylbenzyl)-3-[2-(3-carboxypropenoyl)aminoethoxy]-2-phenylquinoline-4-carboxamideYield 39.6%

Reagents, catalysts & solvents 1

HCID 14798Sodium HydroxideSolvent

Procedure

0.2 g (0.4 mmol) of (S,E)-N-(a-ethylbenzyl)-3-[2-(3-methoxycarbonylpropenoyl) aminoethoxy]-2-phenylquinoline-4-carboxamide (compound of Example 18) were dissolved in 25 ml of 10% NaOH and 5 ml of 1,4-dioxane and warmed to 60° C. for 15 minutes. After cooling, the reaction mixture was extracted with CH2Cl2 and washed with 10% citric acid and sat. sol. NaCl. The organic layer was dried over Na2SO4, evaporated in vacuo to dryness and triturated with i-Pr2O to yield 83 mg of the title compound.

Workup

  1. temperatureAfter cooling
  2. extractionthe reaction mixture was extracted with CH2Cl2
  3. washwashed with 10% citric acid and sat. sol. NaCl
  4. dry with materialThe organic layer was dried over Na2SO4
  5. customevaporated in vacuo to dryness
  6. customtriturated with i-Pr2O

Sources & evidence

ORD record
ord-ce9d89501bfd44f5855a7317dff03e5d
Source dataset
uspto-grants-2001_08
Patent number
US06277862B1

Reaction notes

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