Hydrochloric Acid → HCID 10231798, compound

HRID 488882Notes

Reaction equation

HRID 488882 reaction equation
[Cl:1][C:2]1[CH:11]=[C:10]2[C:5]([C:6]([C:28]3[CH:29]=[C:30](/[CH:34]=[CH:35]/[C:36]([O:38]CC)=[O:37])[CH:31]=[CH:32][CH:33]=3)=[C:7]([CH2:13][C:14]([NH:16][C:17]3[CH:22]=[CH:21][C:20]([Cl:23])=[CH:19][C:18]=3[C:24]([F:27])([F:26])[F:25])=[O:15])[C:8](=[O:12])[O:9]2)=[CH:4][C:3]=1[CH3:41].[OH-].[Na+].Cl>C(O)C.C1COCC1>[Cl:1][C:2]1[CH:11]=[C:10]2[C:5]([C:6]([C:28]3[CH:29]=[C:30](/[CH:34]=[CH:35]/[C:36]([OH:38])=[O:37])[CH:31]=[CH:32][CH:33]=3)=[C:7]([CH2:13][C:14]([NH:16][C:17]3[CH:22]=[CH:21][C:20]([Cl:23])=[CH:19][C:18]=3[C:24]([F:25])([F:27])[F:26])=[O:15])[C:8](=[O:12])[O:9]2)=[CH:4][C:3]=1[CH3:41]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 10282279HCID 10282279, compound

Product 1

HCID 10231798HCID 10231798, compoundYield 71.8%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of ethyl (2E)-3-[3-[7-chloro-3-(2-[[4-chloro-2-(trifluoromethyl)phenyl]amino]-2-oxoethyl)-6-methyl-2-oxo-2H-chromen-4-yl]phenyl]-2-propenoate (200 mg) in a mixture of ethanol (5 ml) and THF (2 ml) was combined with a 1 N aqueous solution of sodium hydroxide (3 ml), and stirred at room temperature for 4 hours. After 1 N hydrochloric acid (10 ml) was added, the mixture was extracted with ethyl acetate. The extract was washed with water, dried over magnesium sulfate, and then concentrated. The resultant crude crystal was recrystallized from THF-ethyl acetate to obtain the title compound as a colorless crystal (137 mg, yield: 70%). Melting point: 191-194° C.

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe extract was washed with water
  3. dry with materialdried over magnesium sulfate
  4. concentrationconcentrated
  5. customThe resultant crude crystal was recrystallized from THF-ethyl acetate

Sources & evidence

ORD record
ord-e7d0a8f694ca47d49f1c4e12f4a89609
Source dataset
uspto-grants-2005_12
Patent number
US06974806B2

Reaction notes

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