Sodium Hydroxide → HCID 19004423, compound

HRID 2225762Notes

Reaction equation

HRID 2225762 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 83.1%

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 hot methanol (5 mL) and tetrahydrofuran (10 mL) was treated with 1N sodium hydroxide (3.0 mL) and the mixture was concentrated to remove the organic solvents. The residue, in water, was treated with 2N hydrochloric acid and the mixture was chilled, filtered, and washed with water. The solids were dissolved in a mixture of tetrahydrofuran and dichloromethane, dried (Na2SO4), filtered, and evaporated to give crude product. Crystallization from acetone-hexane provided 0.4 g of purified 4-[N-[2-(2-naphthalenyloxy)ethyl]formamido]-alpha-oxobenzeneacetic acid as a yellow solid, mp 172° C. with decomposition.

Workup

  1. concentrationthe mixture was concentrated
  2. customto remove the organic solvents
  3. additionThe residue, in water, was treated with 2N hydrochloric acid
  4. temperaturethe mixture was chilled
  5. filtrationfiltered
  6. washwashed with water
  7. dissolutionThe solids were dissolved in a mixture of tetrahydrofuran and dichloromethane
  8. dry with materialdried (Na2SO4)
  9. filtrationfiltered
  10. customevaporated
  11. customto give crude product
  12. customCrystallization from acetone-hexane

Sources & evidence

ORD record
ord-7c06e578be0a45ecbd24514d4f3f25d6
Source dataset
uspto-grants-1994_09
Patent number
US05344843

Reaction notes

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