Sodium Hydroxide → HCID 19004307, compound

HRID 2225737Notes

Reaction equation

HRID 2225737 reaction equation
C[O:2][C:3](=[O:29])[C:4](=[O:28])[C:5]1[CH:10]=[CH:9][C:8]([O:11][CH2:12][CH2:13][CH2:14][NH:15][C:16]([C:18]2[CH:27]=[CH:26][C:25]3[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=3)[CH:19]=2)=[O:17])=[CH:7][CH:6]=1.[OH-].[Na+]>CO.O1CCCC1.O>[CH:19]1[C:20]2[C:25](=[CH:24][CH:23]=[CH:22][CH:21]=2)[CH:26]=[CH:27][C:18]=1[C:16]([NH:15][CH2:14][CH2:13][CH2:12][O:11][C:8]1[CH:7]=[CH:6][C:5]([C:4](=[O:28])[C:3]([OH:29])=[O:2])=[CH:10][CH:9]=1)=[O:17]

Participants

6

Reactant 2

HCID 14798Sodium HydroxideHCID 53708776HCID 53708776, compound

Product 1

HCID 19004307HCID 19004307, compoundYield 58.7%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 4-[[3-(2-naphthoylamino)propyl]oxy]-alpha-oxobenzeneacetic acid methyl ester (0.76 g) in hot methanol (10 mL) and sufficient tetrahydrofuran to dissolve the solids was treated with 1N sodium hydroxide (4.0 mL) and diluted with water. The organic solvent was removed under vacuum and the residue was mixed with water, acidified with excess 2N hydrochloric acid, and extracted with dichloromethane. The organic layer was dried (Na2SO4), filtered, and evaporated to give crude product. Crystallization from acetone-hexane provided 0.43 g of 4-[[3-(2-naphthoylamino) propyl]oxy]-alpha-oxobenzeneacetic acid as a colorless solid, mp 169°-170° C.

Workup

  1. dissolutionto dissolve the solids
  2. customThe organic solvent was removed under vacuum
  3. additionthe residue was mixed with water
  4. extractionextracted with dichloromethane
  5. dry with materialThe organic layer was dried (Na2SO4)
  6. filtrationfiltered
  7. customevaporated
  8. customto give crude product
  9. customCrystallization from acetone-hexane

Sources & evidence

ORD record
ord-1348c10a2f684135927662cf0cd7a96b
Source dataset
uspto-grants-1994_09
Patent number
US05344843

Reaction notes

Loading…