Hydrochloric Acid → 1-(5-Chloropyridin-2-yl)ethan-1-one

HRID 54510

Reaction equation

HRID 54510 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([Cl:8])=[CH:4][N:3]=1.C([Li])CCC.CN(C)[C:16](=[O:18])[CH3:17].Cl>C(OCC)C.C1COCC1.O>[C:16]([C:2]1[CH:7]=[CH:6][C:5]([Cl:8])=[CH:4][N:3]=1)(=[O:18])[CH3:17]

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 31374DimethylacetamideHCID 8170982-Bromo-5-chloropyridineHCID 178418339Butyllithium

Product 1

HCID 101541661-(5-Chloropyridin-2-yl)ethan-1-one

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a suspension of 56 g of 2-bromo-5-chloropyridine in 560 ml of dry diethylether is added a solution of 179 ml of n-butyllithium (15% solution in hexane) at -78° and under argon at such a rate that the temperature never exceeds -72°. Immediately thereafter the solution of 25.7 ml of N,N-dimethylacetamide in dry THF is added. The mixture is stirred for one hour at the same temperature and thereafter decomposed by careful addition of 100 ml of 3N hydrochloric acid, followed by 100 ml of water with vigorous cooling. Working up by process A (see Example 1) and purification by chromatogrphy over silica gel (toluene/ethyl acetate=20/1) yields the compound as white needles; m.p.: 58°-65°.

Workup

  1. customthat the temperature never exceeds -72°
  2. customA (see Example 1) and purification by chromatogrphy over silica gel (toluene/ethyl acetate=20/1)

Sources & evidence

ORD record
ord-7dc9fd34c3da4470aeca855928a96ee5
Source dataset
uspto-grants-1997_04
Patent number
US05622982

Linked notes

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