Pyridine → HCID 13079835, compound

HRID 2418647Notes

Reaction equation

HRID 2418647 reaction equation
[C:1]([OH:5])([CH3:4])([CH3:3])[CH3:2].N1C=CC=CC=1.Cl.[Cl:13][C:14]1[CH:19]=[CH:18][C:17]([C:20]2[CH:21]=[C:22]([C:27](Cl)=[O:28])[C:23]([CH3:26])=[N:24][CH:25]=2)=[CH:16][CH:15]=1.CC(C)([O-])C.[K+]>C(Cl)Cl>[Cl:13][C:14]1[CH:19]=[CH:18][C:17]([C:20]2[CH:21]=[C:22]([C:27]([O:5][C:1]([CH3:4])([CH3:3])[CH3:2])=[O:28])[C:23]([CH3:26])=[N:24][CH:25]=2)=[CH:16][CH:15]=1

Participants

6

Reactant 4

HCID 1049PyridineHCID 6386tert-ButanolHCID 20444701HCID 20444701, compoundHCID 23665647Potassium tert-butoxide

Product 1

HCID 13079835HCID 13079835, compoundYield 20.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Tert-butanol (1.08 g) and dry pyridine (1.31 g) in dry methylene dichloride (20 ml) were added dropwise to the product (2 g) of Stage 1 in dry methylene dichloride (40 ml). After stirring at room temperature for 2 hours, potassium tert-butoxide (1 g) was added and stirring was continued for a further hour. The mixture was washed twice with water, dried and filtered through a bed of activated charcoal and silica. Concentration of the filtrate gave the title product (0.42 g), m.p. 70°-72°.

Workup

  1. stirringstirring
  2. waitwas continued for a further hour
  3. washThe mixture was washed twice with water
  4. customdried
  5. filtrationfiltered through a bed of activated charcoal and silica

Sources & evidence

ORD record
ord-ee9ebb3d755c40b0ad8d1dec990259c6
Source dataset
uspto-grants-1984_09
Patent number
US04473395

Reaction notes

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