Sodium Hydroxide → HCID 19004423, compound

HRID 2225761Notes

Reaction equation

HRID 2225761 reaction equation
C[O:2][C:3](=[O:28])[C:4](=[O:27])[C:5]1[CH:10]=[CH:9][C:8]([N:11]([CH2:14][CH2:15][O:16][C:17]2[CH:26]=[CH:25][C:24]3[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=3)[CH:18]=2)[CH:12]=[O:13])=[CH:7][CH:6]=1.[OH-].[Na+]>CO.O1CCCC1>[CH:18]1[C:19]2[C:24](=[CH:23][CH:22]=[CH:21][CH:20]=2)[CH:25]=[CH:26][C:17]=1[O:16][CH2:15][CH2:14][N:11]([C:8]1[CH:7]=[CH:6][C:5]([C:4](=[O:27])[C:3]([OH:28])=[O:2])=[CH:10][CH:9]=1)[CH:12]=[O:13]

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 53728891HCID 53728891, compound

Product 1

HCID 19004423HCID 19004423, compoundYield 66.5%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of 4-[N-[2-(2-naphthalenyloxy)ethyl]formamido]-alpha-oxobenzeneacetic acid methyl ester (0.5 g) in warm methanol (5 mL) and tetrahydrofuran (5 mL) was treated with 1N sodium hydroxide (2 mL) and the mixture was concentrated to remove the organic solvents. The residue was acidified with excess hydrochloric acid and extracted with dichloromethane. The organic layer was washed with water, dried (Na2SO4), filtered and evaporated. The residue was crystallized acetone-hexane to give 0.32 g of 4-[N-[2-(2-naphthalenyloxy)ethyl]formamido]-alpha-oxobenzeneacetic acid, mp 155°-156° C. as a yellow solid.

Workup

  1. concentrationthe mixture was concentrated
  2. customto remove the organic solvents
  3. extractionextracted with dichloromethane
  4. washThe organic layer was washed with water
  5. dry with materialdried (Na2SO4)
  6. filtrationfiltered
  7. customevaporated
  8. customThe residue was crystallized acetone-hexane

Sources & evidence

ORD record
ord-5862e897a119492fbb04bdc458f2e0a0
Source dataset
uspto-grants-1994_09
Patent number
US05344843

Reaction notes

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