Hydrochloric Acid → 2,3-Dichloro-5-methylpyridine

HRID 2417734Notes

Reaction equation

HRID 2417734 reaction equation
[CH:1]([C:3](Cl)([CH3:9])[CH2:4][CH:5]([Cl:8])[C:6]#[N:7])=O.[ClH:11]>[Cu].[Ta]>[Cl:11][C:6]1[C:5]([Cl:8])=[CH:4][C:3]([CH3:9])=[CH:1][N:7]=1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 133735942,4-Dichloro-4-methyl-5-oxopentanenitrile

Product 1

HCID 127477612,3-Dichloro-5-methylpyridineYield 64.8%

Reagents, catalysts & solvents 2

HCID 23956TantalumCatalystHCID 23978CopperCatalyst

Procedure

18 g of the 4-formyl-2,4-dichlorovaleronitrile obtained in Example 3(a) and 0.1 g of copper powder are heated in a tantalum autoclave for 5 hours to 150° C. after the introduction of 10 g of dry HCl gas under pressure. After they have cooled, the contents of the autoclave are subjected to steam distillation, affording 10.5 g of 2,3-dichloro-5-methylpyridine in the form of colourless crystals with a melting point of 46°-47° C. 1H-NMR spectrum (100 MHz in CDCl3) in ppm: 8.13 (d, 1H, H on C-6); 7.59 (d, 1H, H on C-4); 2.34 (s, 3H, --CH3).

Workup

  1. temperatureAfter they have cooled
  2. distillationthe contents of the autoclave are subjected to steam distillation

Sources & evidence

ORD record
ord-c7ce290b1ec2476ca0c142b0956e5b6b
Source dataset
uspto-grants-1984_09
Patent number
US04469896

Reaction notes

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