Lithium hydroxide, monohydrate → 2,5-dichloro-4-[3-(4-cyclopropyl-3,4-dihydro-2H-quinoxaline-1-carbonyl)-pyridin-4-yloxy]-benzoic acid

HRID 1967009Notes

Reaction equation

HRID 1967009 reaction equation
C[O:2][C:3](=[O:34])[C:4]1[CH:9]=[C:8]([Cl:10])[C:7]([O:11][C:12]2[CH:17]=[CH:16][N:15]=[CH:14][C:13]=2[C:18]([N:20]2[C:29]3[C:24](=[CH:25][CH:26]=[CH:27][CH:28]=3)[N:23]([CH:30]3[CH2:32][CH2:31]3)[CH2:22][CH2:21]2)=[O:19])=[CH:6][C:5]=1[Cl:33].O.[OH-].[Li+]>O1CCOCC1.O>[Cl:33][C:5]1[CH:6]=[C:7]([O:11][C:12]2[CH:17]=[CH:16][N:15]=[CH:14][C:13]=2[C:18]([N:20]2[C:29]3[C:24](=[CH:25][CH:26]=[CH:27][CH:28]=3)[N:23]([CH:30]3[CH2:31][CH2:32]3)[CH2:22][CH2:21]2)=[O:19])[C:8]([Cl:10])=[CH:9][C:4]=1[C:3]([OH:34])=[O:2]

Participants

5

Reactant 2

HCID 168937Lithium hydroxide, monohydrateHCID 533121122,5-dichloro-4-[3-(4-cyclopropyl-3,4-dihydro-2H-quinoxaline-1-carbonyl)-pyridin-4-yloxy]-benzoic acid methyl ester

Product 1

HCID 673205762,5-dichloro-4-[3-(4-cyclopropyl-3,4-dihydro-2H-quinoxaline-1-carbonyl)-pyridin-4-yloxy]-benzoic acidYield 97.6%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Procedure

To a suspension of 3.68 g (7.38 mmol) 2,5-dichloro-4-[3-(4-cyclopropyl-3,4-dihydro-2H-quinoxaline-1-carbonyl)-pyridin-4-yloxy]-benzoic acid methyl ester (Example 27) in 40 mL dioxane and 40 mL water were added 0.387 g (9.22 mmol) lithium hydroxide mono hydrate. The reaction mixture was stirred 1.5 hours at room temperature upon which a yellow solution formed. Dioxane was removed by evaporation and the resulting suspension was diluted with 50 mL water and the pH was adjusted to 1 using 10 mL 25% aqueous hydrochloric acid. The resulting suspension was stirred for approx. 2 hours at room temperature, filtered, washed with water and dried under high vacuum to give 3.49 g (97%) of the desired compound as a light brown solid. MS (ESI): m/z=484.3 [M+H]+.

Workup

  1. customformed
  2. customDioxane was removed by evaporation
  3. additionthe resulting suspension was diluted with 50 mL water
  4. stirringThe resulting suspension was stirred for approx. 2 hours at room temperature
  5. filtrationfiltered
  6. washwashed with water
  7. customdried under high vacuum

Sources & evidence

ORD record
ord-6ecbd342eed3409abc0702b84fc2ba21
Source dataset
uspto-grants-2013_04
Patent number
US08420647B2

Reaction notes

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