Ammonia → 4-Hydroxy-3-methoxy-5-nitrophenyl 3-pyridyl ketone

HRID 2260202Notes

Reaction equation

HRID 2260202 reaction equation
[N+:1]([O-:4])(O)=[O:2].[N:5]1[CH:10]=[CH:9][CH:8]=[C:7]([C:11]([C:13]2[CH:18]=[CH:17][C:16]([OH:19])=[C:15]([O:20][CH3:21])[CH:14]=2)=[O:12])[CH:6]=1.N>C(O)(=O)C>[N:5]1[CH:10]=[CH:9][CH:8]=[C:7]([C:11]([C:13]2[CH:18]=[C:17]([N+:1]([O-:4])=[O:2])[C:16]([OH:19])=[C:15]([O:20][CH3:21])[CH:14]=2)=[O:12])[CH:6]=1

Participants

5

Reactant 3

HCID 222AmmoniaHCID 944Nitric AcidHCID 179776754-Hydroxy-3-methoxyphenyl 3-pyridyl ketone

Product 1

HCID 214591634-Hydroxy-3-methoxy-5-nitrophenyl 3-pyridyl ketone

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

da) 0.38 ml of 65 percent nitric acid is added dropwise at room temperature to 1.15 g of 4-hydroxy-3-methoxyphenyl 3-pyridyl ketone dissolved in 15 ml of acetic acid. After stirring for 2 hours, the reaction mixture is poured into 120 ml of ice-water, whereupon the mixture is adjusted to pH 5 with conc. ammonia and the precipitate formed is filtered off. The thus-obtained residue is heated under reflux in 20 ml of acetonitrile, whereupon it is again filtered off. There is obtained 4-hydroxy-3-methoxy-5-nitrophenyl 3-pyridyl ketone as brown crystals of m.p. 193°.

Workup

  1. customthe precipitate formed
  2. filtrationis filtered off
  3. temperatureThe thus-obtained residue is heated
  4. temperatureunder reflux in 20 ml of acetonitrile, whereupon it
  5. filtrationis again filtered off

Sources & evidence

ORD record
ord-e833818b2b1f4fe5868308b3393e9153
Source dataset
uspto-grants-1995_12
Patent number
US05476875

Reaction notes

Loading…