Dichloromethane → HCID 88404300, compound

HRID 2225864Notes

Reaction equation

HRID 2225864 reaction equation
C[O:2][C:3](=[O:30])/[C:4](=[N:25]/[NH:26][C:27]([NH2:29])=[O:28])/[C:5]1[CH:10]=[CH:9][C:8]([O:11][CH2:12][CH2:13][O:14][C:15]2[CH:24]=[CH:23][C:22]3[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=3)[CH:16]=2)=[CH:7][CH:6]=1.[OH-].[Na+].ClCCl>CO.O1CCCC1.O>[NH2:29][C:27]([NH:26]/[N:25]=[C:4](\[C:5]1[CH:6]=[CH:7][C:8]([O:11][CH2:12][CH2:13][O:14][C:15]2[CH:24]=[CH:23][C:22]3[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=3)[CH:16]=2)=[CH:9][CH:10]=1)/[C:3]([OH:30])=[O:2])=[O:28]

Participants

7

Reactant 3

HCID 6344DichloromethaneHCID 14798Sodium HydroxideHCID 88404110HCID 88404110, compound

Product 1

HCID 88404300HCID 88404300, compoundYield 55.7%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

A mixture of (E)-alpha-[(aminocarbonyl)hydrazono]-4-[2-(2-naphthalenyloxy) ethoxy]benzeneacetic acid methyl ester (0.45 g) in warm methanol (3 mL) and tetrahydrofuran (10 mL) was treated with 1N sodium hydroxide (1.25 mL) and after 30 minutes the mixture was diluted with water and concentrated to remove the organic solvents. The residue was acidified with excess hydrochloric acid and extracted with a dichloromethane-tetrahydrofuran mixture. The organic layer was washed with water, dried (Na2SO4), filtered and evaporated to give crude product. Trituration from dichloromethane provided 0.242 g of pure (E)-alpha-[(aminocarbonyl)hydrazono]- 4-[2-(2-naphthalenyloxy)ethoxy]benzeneacetic acid as a colorless solid, mp 204° C. with decomposition.

Workup

  1. concentrationconcentrated
  2. customto remove the organic solvents
  3. extractionextracted with a dichloromethane-tetrahydrofuran mixture
  4. washThe organic layer was washed with water
  5. dry with materialdried (Na2SO4)
  6. filtrationfiltered
  7. customevaporated
  8. customto give crude product

Sources & evidence

ORD record
ord-2f5760cb0fee446f9276661320f79cde
Source dataset
uspto-grants-1994_09
Patent number
US05344843

Reaction notes

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