Hydrochloric Acid → 2-Chloro-5-ethylpyridine

HRID 2066885Notes

Reaction equation

HRID 2066885 reaction equation
O=P(Cl)(Cl)Cl.[CH2:6]([N:13](/[CH:17]=[CH:18]/[CH2:19][CH3:20])C(=O)C)[C:7]1[CH:12]=CC=CC=1.[ClH:21]>CN(C=O)C>[Cl:21][C:6]1[CH:7]=[CH:12][C:18]([CH2:19][CH3:20])=[CH:17][N:13]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 24813Phosphorus oxychlorideHCID 13494620N-Benzyl-N-((E)-but-1-enyl)-acetamide

Product 1

HCID 111263632-Chloro-5-ethylpyridineYield 19%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Conditions

Temperature
100 °C

Procedure

To DMF (3.8 mL) at 5° C., was added POCl3 (1.4 mL) dropwise. After 5 minutes, 62b (1 g, 4.9 mmol) was added dropwise in 2 mL of DMF. The mixture was heated to 100° C. overnight. The mixture was allowed to cool to room temperature and was added dropwise to 50 mL of 1N HCl. The solution was extracted 3 times with ethyl acetate. The combined organic layer was dried, evaporated, then purified by column chromatography (eluent: 0 to 30% EtOAc in hexane) to give 0.13 g of 62c (19% yield).

Workup

  1. temperatureto cool to room temperature
  2. extractionThe solution was extracted 3 times with ethyl acetate
  3. customThe combined organic layer was dried
  4. customevaporated
  5. custompurified by column chromatography (eluent: 0 to 30% EtOAc in hexane)

Sources & evidence

ORD record
ord-9f22f05713af4ab084ba56ced7a2109c
Source dataset
uspto-grants-2012_10
Patent number
US08293729B2

Reaction notes

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