2-Methylpyridine → HCID 4738497, compound

HRID 968225Notes

Reaction equation

HRID 968225 reaction equation
[NH2:1][C:2]1[N:7]=[C:6]([S:8][CH2:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=2[F:16])[N:5]=[C:4](O)[CH:3]=1.N1C=CC=CC=1C.O=P(Cl)(Cl)[Cl:27]>>[Cl:27][C:4]1[N:5]=[C:6]([S:8][CH2:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=2[F:16])[N:7]=[C:2]([NH2:1])[CH:3]=1

Participants

4

Reactant 3

HCID 79752-MethylpyridineHCID 24813Phosphorus oxychlorideHCID 178507955HCID 178507955, compound

Product 1

HCID 4738497HCID 4738497, compound

Procedure

The product of example 4, step (a) (34 g) was added to a solution of 2-picoline (20 ml) in POCl3 (150 ml) and the mixture refluxed for 24 hr. The reaction mixture was concentrated in vacuo to half its original volume and poured onto ice and then neutralized with ammonia, forming a brown gum. The aqueous phase was decanted off, and the organic residues dissolved in ethyl acetate. This solution was recombined with the aqueous phase, and refluxed for 1 hr. The organic phase was separated, evaporated, and the residue purified by silica gel chromatography, eluting with dichloromethane to afford the subtitled compound as a pale yellow solid (15.6 g).

Workup

  1. temperaturethe mixture refluxed for 24 hr
  2. concentrationThe reaction mixture was concentrated in vacuo to half its original volume
  3. additionpoured onto ice
  4. customforming a brown gum
  5. customThe aqueous phase was decanted off
  6. dissolutionthe organic residues dissolved in ethyl acetate
  7. temperaturerefluxed for 1 hr
  8. customThe organic phase was separated
  9. customevaporated
  10. customthe residue purified by silica gel chromatography
  11. washeluting with dichloromethane

Sources & evidence

ORD record
ord-8d9b6ac0d4bd48c39b759f7e5857d884
Source dataset
uspto-grants-2005_10
Patent number
US06958344B2

Reaction notes

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