Sodium Hydroxide → HCID 18321834, compound

HRID 613633Notes

Reaction equation

HRID 613633 reaction equation
[Cl:1][C:2]1[C:7]([CH2:8][O:9][C:10]2[CH:11]=[CH:12][CH:13]=[C:14]3[C:19]=2[N:18]=[C:17]([CH3:20])[CH:16]=[C:15]3[N:21]2[CH:25]=[CH:24][CH:23]=[N:22]2)=[C:6]([Cl:26])[CH:5]=[CH:4][C:3]=1[N:27]1[CH:31]=[CH:30][CH:29]=[C:28]1[C:32]([O:34]CC)=[O:33].[OH-].[Na+]>O1CCOCC1>[C:32]([C:28]1[N:27]([C:3]2[CH:4]=[CH:5][C:6]([Cl:26])=[C:7]([CH2:8][O:9][C:10]3[CH:11]=[CH:12][CH:13]=[C:14]4[C:19]=3[N:18]=[C:17]([CH3:20])[CH:16]=[C:15]4[N:21]3[CH:25]=[CH:24][CH:23]=[N:22]3)[C:2]=2[Cl:1])[CH:31]=[CH:30][CH:29]=1)([OH:34])=[O:33]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 18321800HCID 18321800, compound

Product 1

HCID 18321834HCID 18321834, compoundYield 79.2%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

To a solution of 1-[2,4-dichloro-3-[2-methyl-4-(pyrazol-1-yl)quinolin-8-yloxymethyl]phenyl]-2-ethoxycarbonylpyrrole (395 mg) in 1,4-dioxane (5 ml) was added 1N sodium hydroxide solution (1.8 ml), and the mixture was refluxed for 2 days. The solvent was removed in vacuo and the residue was dissolved in water. The aqueous solultion was washed with diethyl ether and adjusted to pH 5 with 1N hydrochloric acid. The mixture was extracted with chloroform, and the extract was dried over magnesium sulfate and evaporated in vacuo to give 2-carboxy-1-[2,4-dichloro-3-[2-methyl-4-(pyrazol-1-yl)quinolin-8-yloxymethyl]phenyl]pyrrole (296 mg) as amorphous powder.

Workup

  1. temperaturethe mixture was refluxed for 2 days
  2. customThe solvent was removed in vacuo
  3. dissolutionthe residue was dissolved in water
  4. washThe aqueous solultion was washed with diethyl ether
  5. extractionThe mixture was extracted with chloroform
  6. dry with materialthe extract was dried over magnesium sulfate
  7. customevaporated in vacuo

Sources & evidence

ORD record
ord-fefdf82d55eb416eae9aa7faed43cb6c
Source dataset
uspto-grants-1999_12
Patent number
US06008229

Reaction notes

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