Sodium Hydroxide → HCID 9974136, compound

HRID 1647452Notes

Reaction equation

HRID 1647452 reaction equation
[C:1]([C:6]1[CH:7]=[N:8][C:9]2[C:14]([C:15]=1[NH:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=1[CH3:23])=[CH:13][C:12]([CH2:24][O:25]C(=O)C1C=CC=CC=1)=[CH:11][CH:10]=2)(=[O:5])[CH2:2][CH2:3][CH3:4].[OH-].[Na+]>CO>[C:1]([C:6]1[CH:7]=[N:8][C:9]2[C:14]([C:15]=1[NH:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=1[CH3:23])=[CH:13][C:12]([CH2:24][OH:25])=[CH:11][CH:10]=2)(=[O:5])[CH2:2][CH2:3][CH3:4]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 19923006HCID 19923006, compound

Product 1

HCID 9974136HCID 9974136, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

3-Butyryl-4-(2-methylphenylamino)-6-benzoyloxymethyl-quinoline (3.0 g, 6.8 mmol) was dissolved in methanol (50 ml) and 2M sodium hydroxide solution (50 ml) was added. The mixture was heated under reflux for 45 minutes until a clear solution was obtained. The mixture was partitioned between chloroform and water, the aqueous layer re-extracted with chloroform and the combined organic solutions washed with brine, dried, filtered and evaporated. Crystallisation from ether afforded 3-butyryl-4-(2-methylphenylamino)-6-hydroxymethylquinoline; (1.9 g, 83%), m.p. 139°-41° C.

Workup

  1. temperatureThe mixture was heated
  2. temperatureunder reflux for 45 minutes until a clear solution
  3. customwas obtained
  4. customThe mixture was partitioned between chloroform and water
  5. extractionthe aqueous layer re-extracted with chloroform
  6. washthe combined organic solutions washed with brine
  7. customdried
  8. filtrationfiltered
  9. customevaporated
  10. customCrystallisation from ether

Sources & evidence

ORD record
ord-ab848cb3fb454512b1a6e493c0449454
Source dataset
uspto-grants-1995_07
Patent number
US05432182

Reaction notes

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