Nitric Acid → HCID 178526499, compound

HRID 2379395Notes

Reaction equation

HRID 2379395 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:9]=[N:10][C:11]([Cl:15])=[CH:12][C:13]=2[OH:14])=[CH:4][CH:3]=1.[N+:16]([O-])([OH:18])=[O:17]>>[N+:16]([C:7]1[CH:6]=[C:5]([C:8]2[N:9]=[N:10][C:11]([Cl:15])=[CH:12][C:13]=2[OH:14])[CH:4]=[CH:3][C:2]=1[Cl:1])([O-:18])=[O:17]

Participants

3

Reactant 2

HCID 944Nitric AcidHCID 178516196HCID 178516196, compound

Product 1

HCID 178526499HCID 178526499, compound

Conditions

Temperature
0 °C

Procedure

3-(4'-Chlorophenyl)-4-hydroxy-6-chloropyridazine (12 g, 0.04978 mol) was introduced into cooled, highly-concentrated nitric acid in the course of 15 minutes at a temperature of 0°-5° C. The mixture was stirred for 30 more minutes at 0° C., and the reaction mixture was then stirred into ice-water. The resulting yellow solid product was isolated, washed with water and reprecipitated using NH4OH/HCl. After drying, 11 g, 0.0385 mol, of 3-(3'-nitro-4'-chlorophenyl)-4-hydroxy-6-chloropyridazine of m.p. 204°-209° C. were obtained, which corresponds to a crude yield of 77.25%. According to TLC analysis (SiO2 /10% ethanol/chloroform), the sample proves to be largely uniform. Recrystallized from ethanol, the compound melts at 208°-211° C.

Workup

  1. temperatureinto cooled
  2. customin the course of 15 minutes
  3. customat a temperature of 0°-5° C
  4. customThe resulting yellow solid product was isolated
  5. washwashed with water
  6. customreprecipitated
  7. customAfter drying

Sources & evidence

ORD record
ord-b3800ee7dd7f4048b479903c9dd31140
Source dataset
uspto-grants-1994_11
Patent number
US05362708

Reaction notes

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