Nitric Acid → HCID 135706151, compound

HRID 1060021Notes

Reaction equation

HRID 1060021 reaction equation
Cl.[CH3:2][O:3][C:4]1[CH:9]=[CH:8][N:7]=[C:6]([C:10]2[CH:15]=[CH:14][C:13]([OH:16])=[CH:12][CH:11]=2)[CH:5]=1.[N+:17]([O-])([OH:19])=[O:18].C(=O)([O-])O.[Na+]>C(O)(=O)C>[CH3:2][O:3][C:4]1[CH:9]=[CH:8][N:7]=[C:6]([C:10]2[CH:15]=[CH:14][C:13]([OH:16])=[CH:12][C:11]=2[N+:17]([O-:19])=[O:18])[CH:5]=1

Participants

5

Reactant 3

HCID 944Nitric AcidHCID 516892Sodium BicarbonateHCID 136388330HCID 136388330, compound

Product 1

HCID 135706151HCID 135706151, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
40 °C

Procedure

To a suspension of 4-(4-methoxypyridin-2-yl)phenol hydrochloride (500 mg) in acetic acid (5 ml) was added fuming nitric acid (0.09 ml), and the mixture was stirred at 40° C. for 1 hour. The reaction mixture was poured into a saturated aqueous sodium hydrogencarbonate solution and extracted with ethyl acetate. The separated organic layer was washed with water and brine, dried over sodium sulfate and evaporated under reduced pressure. The residue was triturated with diisopropyl ether, filtered, washed with diisopropyl ether and dried under reduced pressure to give 4-(4-methoxypyridin-2-yl)-3-nitrophenol (293 mg).

Workup

  1. extractionextracted with ethyl acetate
  2. washThe separated organic layer was washed with water and brine
  3. dry with materialdried over sodium sulfate
  4. customevaporated under reduced pressure
  5. customThe residue was triturated with diisopropyl ether
  6. filtrationfiltered
  7. washwashed with diisopropyl ether
  8. customdried under reduced pressure

Sources & evidence

ORD record
ord-a4726b1126f844e599814dff8c757dcb
Source dataset
uspto-grants-2003_02
Patent number
US06521643B1

Reaction notes

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