Nitric Acid → 4-(2-Methylamino-pyrimidin-4-yloxy)-2-nitro-phenol

HRID 491660Notes

Reaction equation

HRID 491660 reaction equation
[CH3:1][NH:2][C:3]1[N:8]=[C:7]([O:9][C:10]2[CH:15]=[CH:14][C:13]([OH:16])=[CH:12][CH:11]=2)[CH:6]=[CH:5][N:4]=1.[N+:17]([O-])([OH:19])=[O:18].C([O-])(O)=O.[Na+]>CC(O)=O.O>[CH3:1][NH:2][C:3]1[N:8]=[C:7]([O:9][C:10]2[CH:15]=[CH:14][C:13]([OH:16])=[C:12]([N+:17]([O-:19])=[O:18])[CH:11]=2)[CH:6]=[CH:5][N:4]=1

Participants

6

Reactant 3

HCID 944Nitric AcidHCID 516892Sodium BicarbonateHCID 177565984-(2-Methylamino-pyrimidin-4-yloxy)-phenol

Product 1

HCID 177550144-(2-Methylamino-pyrimidin-4-yloxy)-2-nitro-phenol

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 962WaterSolvent

Procedure

4-(2-Methylamino-pyrimidin-4-yloxy)-phenol (Step C, 0.20 g, 0.92 mmol) was dissolved in 5 mL AcOH at RT. Fuming HNO3 (0.064 g, 0.92 mmol) was diluted with about 0.012 mL water, then added dropwise over 1 min to the reaction. The reaction was stirred for 18 h, after which it was added slowly to 40 mL saturated aqueous NaHCO3 and extracted with CH2Cl2. The organic layer was washed with NaHCO3 and brine, dried over Na2SO4, filtered, and concentrated in vacuo. The crude residue was purified by silica gel column chromatography using hexanes/EtOAc gradient to yield the title compound. MS (MH+)=263.1; Calc'd 262.23 for C11H10N4O4.

Workup

  1. additionadded dropwise over 1 min to the reaction
  2. extractionextracted with CH2Cl2
  3. washThe organic layer was washed with NaHCO3 and brine
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe crude residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-860a34310c3c4f4bafee8a4b3b21e69e
Source dataset
uspto-grants-2009_05
Patent number
US07531553B2

Reaction notes

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