Hydrochloric Acid → Ethyl 2-chloro-4-methylnicotinate

HRID 369456Notes

Reaction equation

HRID 369456 reaction equation
[ClH:1].C([C:4](=[C:10]([CH3:16])[CH:11]=[CH:12][N:13](C)[CH3:14])[C:5]([O:7][CH2:8][CH3:9])=[O:6])#N>C(O)C>[Cl:1][C:14]1[N:13]=[CH:12][CH:11]=[C:10]([CH3:16])[C:4]=1[C:5]([O:7][CH2:8][CH3:9])=[O:6]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 54385987Ethyl 2-cyano-5-dimethylamino-3-methylpenta-2,4-dienoate

Product 1

HCID 11769512Ethyl 2-chloro-4-methylnicotinateYield 30.4%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Hydrogen chloride was introduced to a stirred mixture of 164 g (0.839 mole) of crude ethyl 2-cyano-5-(N,N-dimethylamino)-3-methyl-2,4-pentadienoate (5) in 500 mL ethanol at 20-45° C. The mixture was stirred at ambient temperature overnight, then heated to reflux for 8 hours. The ethanol was removed under reduced pressure and the residue distilled under high vacuum at 84-94° C., to give 47.7 g (30.4%) of a yellow oil, MH+ 200, NMR (CDCl3), ppm: 1.42 (t,3H); 2.36 (s,3H); 4.46 (q,2H); 7.12 (d,lH); 8.28 (d,1H).

Workup

  1. temperatureheated
  2. temperatureto reflux for 8 hours
  3. customThe ethanol was removed under reduced pressure
  4. distillationthe residue distilled under high vacuum at 84-94° C.

Sources & evidence

ORD record
ord-6fe732dcfbd649009cf6be5308d74cdb
Source dataset
uspto-grants-2000_10
Patent number
US06136982

Reaction notes

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