Pyridine → HCID 19843735, compound

HRID 2352130Notes

Reaction equation

HRID 2352130 reaction equation
N1C=CC=CC=1.[CH:7]1([CH:10]([C:12]2[CH:13]=[N:14][CH:15]=[N:16][CH:17]=2)[OH:11])[CH2:9][CH2:8]1.CCOCC>ClCCl.[O-2].[Cr+6].[O-2].[O-2]>[N:14]1[CH:13]=[C:12]([C:10]([CH:7]2[CH2:8][CH2:9]2)=[O:11])[CH:17]=[N:16][CH:15]=1

Participants

6

Reactant 3

HCID 1049PyridineHCID 3283Diethyl EtherHCID 19843738HCID 19843738, compound

Product 1

HCID 19843735HCID 19843735, compound

Reagents, catalysts & solvents 2

HCID 10219390chromium (VI) trioxideCatalystHCID 6344DichloromethaneSolvent2×

Procedure

To a suspension of chromium (VI) oxide (42.4 g, 0.41 mol) in dry dichloromethane (1000 ml) was added dry pyridine (66 ml, 0.825 mol) and the mixture was stirred for half an hour. A solution of the product of Stage 1 (10 g, 66 mmol) in dry dichloromethane (125 ml) was then added dropwise with stirring. After 2 hours, the reaction mixture was poured into ether and filtered. The filtrate was washed with copper sulphate solution, and brine and then dried over magnesiums sulphate before removing the solvent. Flash chromatography gave the product as a pale yellow oil.

Workup

  1. stirringwith stirring
  2. filtrationfiltered
  3. washThe filtrate was washed with copper sulphate solution, and brine
  4. dry with materialdried over magnesiums sulphate
  5. custombefore removing the solvent

Sources & evidence

ORD record
ord-dedf5c12f67d43e6a37e8fdf0f171187
Source dataset
uspto-grants-1989_10
Patent number
US04875922

Reaction notes

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