Nitric Acid → HCID 178526598, compound

HRID 384314Notes

Reaction equation

HRID 384314 reaction equation
[NH:1]1[C:5]([C:6]2[CH:7]=[C:8]([C:12]3[C:13]([OH:18])=[CH:14][CH:15]=[CH:16][CH:17]=3)[CH:9]=[CH:10][CH:11]=2)=[N:4][N:3]=[N:2]1.[N+:19]([O-])([OH:21])=[O:20].O>C(O)C>[N+:19]([C:14]1[CH:15]=[CH:16][CH:17]=[C:12]([C:8]2[CH:9]=[CH:10][CH:11]=[C:6]([C:5]3[NH:1][N:2]=[N:3][N:4]=3)[CH:7]=2)[C:13]=1[OH:18])([O-:21])=[O:20]

Participants

5

Reactant 3

HCID 944Nitric AcidHCID 962WaterHCID 178515935HCID 178515935, compound

Product 1

HCID 178526598HCID 178526598, compoundYield 27%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

3′-(1H-Tetrazol-5-yl)-biphenyl-2-ol 8d (3.5 g, 14.7 mmol) was dissolved in 145 mL of ethanol under argon atmosphere. Fuming nitric acid (0.565 mL, 13.2 mmol) was added dropwise at 35° C. After the reaction mixture was reacted at room temperature for 1 hour, 150 mL of water was added. After standing overnight, the mixture was filtered. The filter cake was washed with 100 mL of water and dissolved in 500 mL of ethyl acetate and 250 mL of water. The separated organic layer was washed with saturated brine and dried over anhydrous magnesium sulfate. The mixture was purified by silica gel column chromatography to obtain the title compound 3-nitro-3′-(1H-tetrazol-5-yl)-biphenyl-2-ol 8e (1 g, yield 27.0%) as a yellow solid.

Workup

  1. customAfter the reaction mixture was reacted at room temperature for 1 hour
  2. filtrationthe mixture was filtered
  3. washThe filter cake was washed with 100 mL of water
  4. dissolutiondissolved in 500 mL of ethyl acetate
  5. washThe separated organic layer was washed with saturated brine
  6. dry with materialdried over anhydrous magnesium sulfate
  7. customThe mixture was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-c733eca858904fa1904e4104c06cd3e2
Source dataset
uspto-grants-2013_02
Patent number
US08367710B2

Reaction notes

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