Sodium Hydroxide → HCID 68418414, compound

HRID 2098585Notes

Reaction equation

HRID 2098585 reaction equation
[CH:1]1([NH:4][C:5](=[O:33])[C:6]([C:15]2[CH:20]=[CH:19][C:18]([NH:21][CH2:22][C:23]3[CH:32]=[CH:31][C:26]([C:27]([O:29]C)=[O:28])=[CH:25][CH:24]=3)=[CH:17][CH:16]=2)=[CH:7][C:8]2[CH:13]=[CH:12][C:11]([F:14])=[CH:10][CH:9]=2)[CH2:3][CH2:2]1.[OH-].[Na+]>CO.O>[CH:1]1([NH:4][C:5](=[O:33])[C:6]([C:15]2[CH:20]=[CH:19][C:18]([NH:21][CH2:22][C:23]3[CH:24]=[CH:25][C:26]([C:27]([OH:29])=[O:28])=[CH:31][CH:32]=3)=[CH:17][CH:16]=2)=[CH:7][C:8]2[CH:13]=[CH:12][C:11]([F:14])=[CH:10][CH:9]=2)[CH2:3][CH2:2]1

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 68416868HCID 68416868, compound

Product 1

HCID 68418414HCID 68418414, compoundYield 56.8%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Conditions

Temperature
70 °C

Procedure

To a solution methyl 4-((4-(3-(cyclopropylamino)-1-(4-fluorophenyl)-3-oxoprop-1-en-2-yl)phenylamino)methyl)benzoate (0.42 g, 0.9 mmol) in methanol (10 mL), a solution of NaOH (0.075 g, 18 mmol) in water (0.5 mL) was added. The reaction mixture was refluxed for 1 hour at 70° C. The solvent was removed by evaporation and the remainder was poured to ice cold water. The aqueous layer was acidified to pH 3 with citric acid and allowed to stand at 4° C. for 30 minutes, the solid precipitated was filtered and dried under vacuum to give a pale yellow solid (0.22 g, 51% yield).

Workup

  1. customThe solvent was removed by evaporation
  2. additionthe remainder was poured to ice cold water
  3. customthe solid precipitated
  4. filtrationwas filtered
  5. customdried under vacuum

Sources & evidence

ORD record
ord-23d18110246f43238a9b88e1ccb8ab0d
Source dataset
uspto-grants-2013_05
Patent number
US08450525B2

Reaction notes

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