Hydrochloric Acid → HCID 20146136, compound

HRID 569715Notes

Reaction equation

HRID 569715 reaction equation
N[C:2]1[C:3]([CH3:8])=[CH:4]C=CC=1.Cl.N([O-])=O.[Na+].[NH2:14][C:15](N)=[O:16].N(O)=O.[NH:21]1[CH:26]=[CH:25][CH:24]=[CH:23][C:22]1=[O:27]>[OH-].[Na+]>[C:15]([NH:14][N:21]1[CH:26]=[CH:25][CH:24]=[CH:23][C:22]1=[O:27])(=[O:16])[C:3]([CH3:8])([CH3:4])[CH3:2]

Participants

8

Reactant 6

HCID 313Hydrochloric Acid2×HCID 1176UreaHCID 7242O-ToluidineHCID 88712-PyridoneHCID 24529Nitrous AcidHCID 23668193Sodium Nitrite

Product 1

HCID 20146136HCID 20146136, compound

Reagents, catalysts & solvents 1

HCID 14798Sodium HydroxideSolvent

Conditions

Temperature
0 °C

Procedure

The toluidine compound was suspended in the HCl, cooled to 0° C. and diazotized by the addition of the NaNO2. Stirring was continued until all the solid was in solution (about 2 hours). Urea was added to decompose any excess nitrous acid. The pyridone compound was dissolved in the NaOH, cooled and the diazo solution added slowly. After 2 hours the mixture was acidified with HCl to pH5 and the dye filtered off and washed with water. Yield: 52 g. Recrystallization from ethanol gave an analytical sample.

Workup

  1. customwas in solution (about 2 hours)
  2. temperaturecooled
  3. filtrationthe dye filtered off
  4. washwashed with water
  5. customRecrystallization from ethanol
  6. customgave an analytical sample

Sources & evidence

ORD record
ord-8325c13a122441f1b6936d6f91dcb2c3
Source dataset
uspto-grants-1988_03
Patent number
US04734349

Reaction notes

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