Hydrochloric Acid → HCID 88404110, compound

HRID 2225863Notes

Reaction equation

HRID 2225863 reaction equation
[CH3:1][O:2][C:3](=[O:26])[C:4](=O)[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.Cl.[NH2:28][NH:29][C:30]([NH2:32])=[O:31].Cl.O/N=C(/C1C=CC(OCCOC2C=CC3C(=CC=CC=3)C=2)=CC=1)\C(O)=O>N1C=CC=CC=1>[CH3:1][O:2][C:3](=[O:26])/[C:4](=[N:28]/[NH:29][C:30]([NH2:32])=[O:31])/[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

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 11236Semicarbazide hydrochlorideHCID 19004464HCID 19004464, compoundHCID 541704664-[2-(2-Naphthalenyloxy)ethoxy]-alpha-oxobenzeneacetic acid methyl ester

Product 1

HCID 88404110HCID 88404110, compoundYield 29.5%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Conditions

Temperature
50 °C

Procedure

A mixture of 4-[2-(2-naphthalenyloxy)ethoxy]-alpha-oxobenzeneacetic acid methyl ester (1.75 g) in pyridine (25 mL) was warmed to dissolve and added semicarbazide hydrochloride (0.7 g). The stirred mixture was heated at 50° C. for 4 hours, cooled, acidified with hydrochloric acid and extracted twice with dichloromethane. The organic layers were washed with dilute hydrochloric acid, combined, dried (Na2SO4), filtered and evaporated to provide a crude mixture of (E) and (Z) isomers. The crude mixture was separated by HPLC (dichloromethane-tetrahydrofuran; 9:1) and the more polar component was crystallized from dichloromethane-methanol to provide 0.6 g of (E)-alpha-[(aminocarbonyl)hydrazono]-4-[2-(2-naphthalenyloxy)ethoxy]benzeneacetic acid methyl ester as a colorless solid, mp 180°-181° C.

Workup

  1. temperaturewas warmed
  2. dissolutionto dissolve
  3. temperaturecooled
  4. extractionextracted twice with dichloromethane
  5. washThe organic layers were washed with dilute hydrochloric acid
  6. dry with materialdried (Na2SO4)
  7. filtrationfiltered
  8. customevaporated
  9. customto provide a crude
  10. customThe crude mixture was separated by HPLC (dichloromethane-tetrahydrofuran; 9:1)
  11. customthe more polar component was crystallized from dichloromethane-methanol

Sources & evidence

ORD record
ord-ef388f3bce9d4984a387fb6f9218ea7e
Source dataset
uspto-grants-1994_09
Patent number
US05344843

Reaction notes

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