Nitric Acid → HCID 58136884, compound

HRID 1524519Notes

Reaction equation

HRID 1524519 reaction equation
[CH2:1]([O:3][C:4]1[CH:5]=[C:6]([NH2:13])[N:7]=[N:8][C:9]=1[O:10][CH2:11][CH3:12])[CH3:2].[N+:14]([O-])([OH:16])=[O:15]>S(=O)(=O)(O)O>[CH2:1]([O:3][C:4]1[CH:5]=[C:6]([NH:13][N+:14]([O-:16])=[O:15])[N:7]=[N:8][C:9]=1[O:10][CH2:11][CH3:12])[CH3:2]

Participants

4

Reactant 2

HCID 944Nitric AcidHCID 66936036HCID 66936036, compound

Product 1

HCID 58136884HCID 58136884, compound

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent2×

Conditions

Temperature
0 °C

Procedure

5,6-Diethoxypyridazin-3-ylamine (analogously to T. Horie in Chemical & Pharmaceutical Bulletin (1963), 11(9), 1157-67; 160 mg) was initially charged dissolved in concentrated sulfuric acid (4 ml) at RT. The mixture was then cooled to 0° C. and 2 ml of a 1:1 mixture of concentrated nitric acid and concentrated sulfuric acid were added dropwise. After 20 min at 0° C., the ice bath was removed and the mixture was stirred for 4 h. Then it was cooled again to 0° C., a further 0.5 ml of the acid mixture was added and the mixture was stirred at 0° C. for another hour. Then it was admixed with ice while cooling with ice. After adding DCM, the phases were separated and extracted three times with DCM. The combined DCM phases were dried over sodium sulfate, filtered and concentrated. 188 mg of the title compound were obtained. LC-MS rt: 0.81 min [M+H]+: 236.2 (met. b)

Workup

  1. addition160 mg) was initially charged
  2. additionwere added dropwise
  3. customthe ice bath was removed
  4. temperatureThen it was cooled again to 0° C.
  5. additiona further 0.5 ml of the acid mixture was added
  6. stirringthe mixture was stirred at 0° C. for another hour
  7. temperaturewhile cooling with ice
  8. additionAfter adding DCM
  9. customthe phases were separated
  10. extractionextracted three times with DCM
  11. dry with materialThe combined DCM phases were dried over sodium sulfate
  12. filtrationfiltered
  13. concentrationconcentrated

Sources & evidence

ORD record
ord-b5e6639158144bce999910ba502619b3
Source dataset
uspto-grants-2015_07
Patent number
US09079906B2

Reaction notes

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