Nitric Acid → HCID 18913970, compound

HRID 362639Notes

Reaction equation

HRID 362639 reaction equation
[Cl:1][C:2]1[C:3]([N:11]2[C:15]([NH:16][C:17](=[O:20])[CH2:18][CH3:19])=[CH:14][CH:13]=[N:12]2)=[N:4][N:5]2[CH2:10][CH2:9][CH2:8][CH2:7][C:6]=12.C(OC(=O)C)(=O)C.[N+:28]([O-])([OH:30])=[O:29]>C(O)(=O)C>[Cl:1][C:2]1[C:3]([N:11]2[C:15]([NH:16][C:17](=[O:20])[CH2:18][CH3:19])=[C:14]([N+:28]([O-:30])=[O:29])[CH:13]=[N:12]2)=[N:4][N:5]2[CH2:10][CH2:9][CH2:8][CH2:7][C:6]=12

Participants

5

Reactant 3

HCID 944Nitric AcidHCID 7918Acetic AnhydrideHCID 53818781HCID 53818781, compound

Product 1

HCID 18913970HCID 18913970, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

8.72 g (29.7 mmol) N-[1-(3-Chloro-4,5,6,7-tetrahydropyrazolo[1,5-a]pyridin-2-yl)-5-pyrazolyl]propionamide was suspended in 33 ml acetic acid. Under ice cooling, at 0°-5° C., 3.31 g (32.5 mmol) acetic anhydride was added. 1.93 g (31 mmol) Fuming nitric acid was added dropwise. After stirring for 6 hours at room temperature, the mixture was concentrated. The residue was taken up in dichloromethane, neutralised with aqueous sodium hydrogen carbonate and washed with aqueous sodium chloride. The organic phase was dried over magnesium sulfate and concentrated. The residue was purified by silica gel chromatography (hexane/ethyl acetate 1:1).

Workup

  1. additionwas added dropwise
  2. concentrationthe mixture was concentrated
  3. washwashed with aqueous sodium chloride
  4. dry with materialThe organic phase was dried over magnesium sulfate
  5. concentrationconcentrated
  6. customThe residue was purified by silica gel chromatography (hexane/ethyl acetate 1:1)

Sources & evidence

ORD record
ord-3029dd5a04024c03bd3598dda13e505f
Source dataset
uspto-grants-1999_02
Patent number
US05869686

Reaction notes

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