Pyridine → HCID 13533705, compound

HRID 465117Notes

Reaction equation

HRID 465117 reaction equation
Cl[C:2]1[N:7]=[CH:6][C:5]([C:8]2[CH:9]=[N:10][CH:11]=[CH:12][CH:13]=2)=[CH:4][CH:3]=1.[NH2:14]N.[N:16]1C=CC=[CH:18][CH:17]=1>>[CH3:18][C:17]1[N:7]2[CH:6]=[C:5]([C:8]3[CH:9]=[N:10][CH:11]=[CH:12][CH:13]=3)[CH:4]=[CH:3][C:2]2=[N:14][N:16]=1

Participants

4

Reactant 3

HCID 1049PyridineHCID 9321HydrazineHCID 10081254HCID 10081254, compound

Product 1

HCID 13533705HCID 13533705, compound

Conditions

Temperature
110 °C

Procedure

A 90 mg portion of 6-chloro-3,3'-bipyridine and 0.15 ml of anhydrous hydrazine were dissolved in 20 ml of pyridine and heated at 110° C. for 48 hours. The volatiles were removed at reduced pressure and the residue dissolved in 20 ml of triethyl orthoacetate and heated at 110° C. for 12 hours. The volatiles were removed at reduced pressure and the residue purified by chromatography on silica gel, eluting with ethyl acetate:methanol (9:2). The obtained tan solid was recrystallized from ethyl acetate-methanol, giving the desired product as off-white flakes, mp 199°-201.5° C.

Workup

  1. customThe volatiles were removed at reduced pressure
  2. dissolutionthe residue dissolved in 20 ml of triethyl orthoacetate
  3. temperatureheated at 110° C. for 12 hours
  4. customThe volatiles were removed at reduced pressure
  5. customthe residue purified by chromatography on silica gel
  6. washeluting with ethyl acetate:methanol (9:2)
  7. customThe obtained tan solid was recrystallized from ethyl acetate-methanol

Sources & evidence

ORD record
ord-5523593def274018af4d0ba2088e1ee8
Source dataset
uspto-grants-1985_10
Patent number
US04550166

Reaction notes

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