Sodium Methoxide → HCID 67409974, compound

HRID 1481563Notes

Reaction equation

HRID 1481563 reaction equation
Cl[C:2]1[C:7]([N+:8]([O-:10])=[O:9])=[C:6]([NH2:11])[CH:5]=[C:4]([C:12]2[C:17]([Cl:18])=[CH:16][CH:15]=[CH:14][C:13]=2[Cl:19])[N:3]=1.[CH3:20][O-:21].[Na+]>CO>[Cl:19][C:13]1[CH:14]=[CH:15][CH:16]=[C:17]([Cl:18])[C:12]=1[C:4]1[N:3]=[C:2]([O:21][CH3:20])[C:7]([N+:8]([O-:10])=[O:9])=[C:6]([NH2:11])[CH:5]=1

Participants

4

Reactant 2

HCID 10942334Sodium MethoxideHCID 86657418HCID 86657418, compound

Product 1

HCID 67409974HCID 67409974, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Conditions

Temperature
65 °C

Procedure

2-Chloro-6-(2,6-dichlorophenyl)-3-nitropyridin-4-ylamine (28.7 mg, 0.0901 mmol, prepared as described in the previous step) was placed in a 8 mL vial equipped with a stir bar and anhydrous MeOH (1 mL) was added via syringe. NaOMe (0.5 M in MeOH, (0.396 mL, 0.198 mmol) was added to the stirred mixture, which was then stirred at 65° C. for 4 h. The solvent was removed under reduced pressure and the residue was chromatographed on a 12-g SiO2 pre-packed column eluting with 0:1-2:3 EtOAc/heptane to yield 6-(2,6-dichlorophenyl)-2-methoxy-3-nitropyridin-4-ylamine. 1H-NMR (400 MHz, CDCl3) δ: 7.37-7.41 (m, 2H), 7.25-7.30 (m, 1H), 6.35 (s, 1H), 6.15 (br. s., 2H), 4.01 (s, 3H).

Workup

  1. customvial equipped with a stir bar
  2. customThe solvent was removed under reduced pressure
  3. customthe residue was chromatographed on a 12-g SiO2 pre-packed column
  4. washeluting with 0:1-2:3 EtOAc/heptane

Sources & evidence

ORD record
ord-21ce15feb80448a7bfd573f9bb2e53c1
Source dataset
uspto-grants-2016_08
Patent number
US09409915B2

Reaction notes

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