Ammonia → HCID 21882700, compound

HRID 722067Notes

Reaction equation

HRID 722067 reaction equation
[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][N:12]=[C:11](F)[C:10]=1[N+:16]([O-:18])=[O:17])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[NH3:19]>CO>[NH2:19][C:11]1[C:10]([N+:16]([O-:18])=[O:17])=[C:9]([O:8][CH2:1][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)[CH:14]=[CH:13][N:12]=1

Participants

4

Reactant 2

HCID 222AmmoniaHCID 21882757HCID 21882757, compound

Product 1

HCID 21882700HCID 21882700, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

0.73 g of 4-benzyloxy-2-fluoro-3-nitropyridine (starting material M3) are dissolved in 10 ml of a 5M solution of ammonia in methanol and stirred at ambient temperature for 16 hours. The solvent is distilled off and the residue is chromatographed on silica gel (dichloromethane/petroleum ether 4:1+1% triethylamine). Concentration of the pure fractions and drying in vacuo gives 0.51 g of the title compound as a yellow solid of m.p. 145–147° C. The mass spectrum shows the molecular peak MH+ at 246.0 Da.

Workup

  1. distillationThe solvent is distilled off
  2. customthe residue is chromatographed on silica gel (dichloromethane/petroleum ether 4:1+1% triethylamine)
  3. customConcentration of the pure fractions and drying in vacuo

Sources & evidence

ORD record
ord-b75a2014a6da43539bb312d75fc1a316
Source dataset
uspto-grants-2006_11
Patent number
US07138399B2

Reaction notes

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