Hydrochloric Acid → Methyl 2,6-dichloropyridine-3-carboxylate
Reaction equation
[Cl:1][C:2]1[N:10]=[C:9]([Cl:11])[CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].Cl.[CH3:13]O>>[Cl:1][C:2]1[N:10]=[C:9]([Cl:11])[CH:8]=[CH:7][C:3]=1[C:4]([O:6][CH3:13])=[O:5]Participants
4
Procedure
19.1 g (0.1 mole) of 2,6-dichloronicotinic acid [Guthzeit and Laska, J. pr. Ch. 58 [2], 425 (1898)] are suspended in 250 ml of methanol and, while stirring and cooling with ice, hydrogen chloride gas is introduced until the mixture is saturated. The reaction mixture is allowed to stand for 48 hours at room temperature and subsequently heated for 3 hours to reflux temperature. It is then evaporated to dryness in a high vacuum at 40° C and the residue is dried in a high vacuum at 40° C. The brown crystalline product is recrystallised from ether-pentane to yield methyl 2,6-dichloronicotinate with a melting point of 53°-54° C.
Workup
- additionis introduced until the mixture
- temperaturesubsequently heated for 3 hours
- temperatureto reflux temperature
- customIt is then evaporated to dryness in a high vacuum at 40° C
- customthe residue is dried in a high vacuum at 40° C
- customThe brown crystalline product is recrystallised from ether-pentane
Sources & evidence
- ORD record
- ord-95708172ff7442229ba3530082695236
- Source dataset
- uspto-grants-1978_05
- Patent number
- US04089960
Reaction notes
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