Hydrochloric Acid → HCID 69945265, compound

HRID 1870944Notes

Reaction equation

HRID 1870944 reaction equation
[CH:1]([C:3]1[CH:12]=[CH:11][C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=1)=O.[C:13]([OH:19])(=[O:18])[CH2:14]C(O)=O.C([O-])(=O)C.[NH4+:24].[ClH:25]>C(O)C>[ClH:25].[NH2:24][CH:1]([C:3]1[CH:12]=[CH:11][C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=1)[CH2:14][C:13]([OH:19])=[O:18]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 867Malonic AcidHCID 62012-NaphthalenecarboxaldehydeHCID 517165Ammonium Acetate

Product 1

HCID 69945265HCID 69945265, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

The method described in J. Am. Chem. Soc., 1936, 58, 299 is used. 15.5 g of 2-formylnaphthalene, 10.4 g of malonic acid and 15.4 g of ammonium acetate in 150 ml of ethanol are mixed together and refluxed for 6 hours. After cooling to RT, the product is drained, washed with EtOH and dried. The product obtained is dissolved in a sufficient amount of 2N HCl and the insoluble material is then filtered off. The acidic solution is concentrated by evaporating under vacuum and the solid thus formed is recrystallized from 20 ml of an AcOH/H2O mixture (1/1; v/v). 3.8 g of the expected product are obtained.

Workup

  1. temperaturerefluxed for 6 hours
  2. washwashed with EtOH
  3. customdried
  4. customThe product obtained
  5. filtrationthe insoluble material is then filtered off
  6. concentrationThe acidic solution is concentrated
  7. customby evaporating under vacuum
  8. customthe solid thus formed
  9. customis recrystallized from 20 ml of an AcOH/H2O mixture (1/1; v/v)

Sources & evidence

ORD record
ord-655226713b7e4512a8b7f584bf9004b5
Source dataset
uspto-grants-2000_08
Patent number
US06100278

Reaction notes

Loading…