Pyridine → HCID 20074920, compound

HRID 1709732Notes

Reaction equation

HRID 1709732 reaction equation
N1C=CC=CC=1.[OH:7][CH:8]([C:10]1[C:20]2=[C:21]3[C:16](=[CH:17][CH:18]=[CH:19]2)[CH2:15][CH2:14][CH2:13][N:12]3[N:11]=1)[CH3:9]>C(Cl)Cl.[O-2].[O-2].[O-2].[Cr+6]>[C:8]([C:10]1[C:20]2=[C:21]3[C:16](=[CH:17][CH:18]=[CH:19]2)[CH2:15][CH2:14][CH2:13][N:12]3[N:11]=1)(=[O:7])[CH3:9]

Participants

5

Reactant 2

HCID 1049PyridineHCID 20074918HCID 20074918, compound

Product 1

HCID 20074920HCID 20074920, compoundYield 87.4%

Reagents, catalysts & solvents 2

HCID 10219390chromium (VI) trioxideCatalystHCID 6344DichloromethaneSolvent2×

Procedure

19.7 g (0.25 mol) of pyridine were dissolved in 335 ml of methylene chloride. 15.2 (152 mmol) of chromium trioxide were added in portions under an atmosphere of nitrogen at temperatures below 35° C., and the mixture was stirred for 30 minutes. 4.0 g (0.02 mol) of 2-(1-hydroxyethyl)-7,8-dihydro-6H-pyrazolo[4,5,1-ij]quinoline (obtained by reaction of 2-formyl-7,8-dihydro-6H-pyrazolo[4,5,1-ij]quinoline with 2.5 equivalent of methylmagnesium bromide), dissolved in 40 ml of methylene chloride were then added. The mixture was stirred for a few minutes, decanted and evaporated in vacuum. The residue was chromatographed over silicagel using methylene chloride/ethyl acetate (3/1) as a eluent. 3.5 g of the desired product were obtained after evaporation of the desired fractions. Melting point 101°-102° C.

Workup

  1. additionwere then added
  2. stirringThe mixture was stirred for a few minutes
  3. customdecanted
  4. customevaporated in vacuum
  5. customThe residue was chromatographed

Sources & evidence

ORD record
ord-d37642a0b8804cfa8283f6420709ecc4
Source dataset
uspto-grants-1990_08
Patent number
US04950759

Reaction notes

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