Water → 2,5-Dichloroisonicotinic acid

HRID 1914604Notes

Reaction equation

HRID 1914604 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([Cl:8])=[CH:4][N:3]=1.C([Li])CCC.CN(C)CCN(C)CCN(C)C.[OH2:26].C1[CH2:31][O:30]CC1>>[Cl:1][C:2]1[CH:7]=[C:6]([C:31]([OH:30])=[O:26])[C:5]([Cl:8])=[CH:4][N:3]=1

Participants

6

Reactant 5

HCID 962WaterHCID 8028TetrahydrofuranHCID 18196PentamethyldiethylenetriamineHCID 276852,5-DichloropyridineHCID 178418339Butyllithium

Product 1

HCID 27360872,5-Dichloroisonicotinic acid

Procedure

At −75° C., 2,5-dichloropyridine (3.7 g) was added to a solution of butyl lithium (25 ml, 1M) and N,N,N′,N″,N″-pentamethyldiethylenetriamine (5.3 ml) in THF (50 ml) under a nitrogen atmosphere at −75° C. and the reaction mixture stirred for 2 h, poured onto dry ice, and water (50 ml) added. The aqueous phase was washed with diethyl ether; acidified to pH 2 and the white solid filtered off dried to give the product (2.5 g), a known compound, for the next reaction, without further characterization other than ascertaining that the compound was one spot by tlc with the expected molecular weight (M−1) of 190.

Workup

  1. additionadded
  2. washThe aqueous phase was washed with diethyl ether
  3. filtrationthe white solid filtered off
  4. customdried

Sources & evidence

ORD record
ord-98b91fc4a7f54f99bb6334a24ad98e1b
Source dataset
uspto-grants-2013_12
Patent number
US08614212B2

Reaction notes

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