Ethanol → 2,6-Dichloro-isonicotinic acid ethyl ester

HRID 1590390Notes

Reaction equation

HRID 1590390 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:8]=[C:9]([Cl:11])[N:10]=1)[C:5]([OH:7])=[O:6].S(=O)(=O)(O)O.[CH2:17](O)[CH3:18]>>[CH2:17]([O:6][C:5](=[O:7])[C:4]1[CH:8]=[C:9]([Cl:11])[N:10]=[C:2]([Cl:1])[CH:3]=1)[CH3:18]

Participants

4

Reactant 3

HCID 702EthanolHCID 1118Sulfuric AcidHCID 948302,6-Dichloroisonicotinic acid

Product 1

HCID 948232,6-Dichloro-isonicotinic acid ethyl ester

Procedure

2,6-Dichloroisonicotinic acid (4.0 g) (prepared according to M. M Robinson, J.Amer.Chem.Soc. 80,5481,1958) was dissolved in ethanol (20 ml) and concentrated sulphuric acid (1 ml). After 6 hours at 80°, the solution was cooled, concentrated in vacuo and the residue worked up in the usual manner to give ethyl-2,6-dichloroisonicotinate (3.7 g). NMR 1H: 7.84(2H,s), 4.48(2H,q), 1.48(3H,t).

Workup

  1. temperaturethe solution was cooled
  2. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-7058d7c3620b4513b652ff7c12f9e90b
Source dataset
uspto-grants-1993_04
Patent number
US05202356

Reaction notes

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