Nitric Acid → HCID 21097332, compound

HRID 2109314Notes

Reaction equation

HRID 2109314 reaction equation
C[O:2][C:3](=[O:23])[C:4]1[CH:9]=[CH:8][C:7]([CH3:10])=[C:6]([N:11]2[CH:15]=[C:14]([C:16]3[CH:17]=[N:18][CH:19]=[CH:20][CH:21]=3)[N:13]=[C:12]2S)[CH:5]=1.[N+]([O-])(O)=O.N([O-])=O.[Na+].[OH-].[Na+]>O.CC(O)=O>[CH3:10][C:7]1[CH:8]=[CH:9][C:4]([C:3]([OH:23])=[O:2])=[CH:5][C:6]=1[N:11]1[CH:15]=[C:14]([C:16]2[CH:17]=[N:18][CH:19]=[CH:20][CH:21]=2)[N:13]=[CH:12]1

Participants

7

Reactant 4

HCID 944Nitric AcidHCID 14798Sodium HydroxideHCID 23668193Sodium NitriteHCID 178497763HCID 178497763, compound

Product 1

HCID 21097332HCID 21097332, compoundYield 22%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 962WaterSolvent

Conditions

Temperature
0 °C

Procedure

To a suspension of 85 mg (0.261 mmol) of 3-(2-mercapto-4-pyridin-3-yl-imidazol-1-yl)-4-methyl-benzoic acid methyl ester in 1.8 mL of water was added 0.68 mL of concentrated HNO3 and 2 mg of NaNO2. After 2 h, the mixture was cooled to 0° C. and 4N NaOH was added until the pH reached about 10. The mixture was stirred for 30 min then HOAc was added until the pH reached about 6. The resulting precipitate was filtered, washed with water and dried to provide 16 mg (0.057 mmol; 22%) of 4-methyl-3-(4-pyridin-3-yl-imidazol-1-yl)-benzoic acid.

Workup

  1. filtrationThe resulting precipitate was filtered
  2. washwashed with water
  3. customdried

Sources & evidence

ORD record
ord-a605670324b145b4be352577953e04b7
Source dataset
uspto-grants-2009_04
Patent number
US07514458B2

Reaction notes

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