Hydrochloric Acid → Ethyl 2-chloro-4-methylnicotinate

HRID 704448Notes

Reaction equation

HRID 704448 reaction equation
C([C:3]([C:11]([O:13][CH2:14][CH3:15])=[O:12])=[C:4]([CH3:10])[CH:5]=[CH:6][N:7](C)[CH3:8])#N.[ClH:16]>C1(C)C=CC=CC=1>[CH2:14]([O:13][C:11](=[O:12])[C:3]1[C:4]([CH3:10])=[CH:5][CH:6]=[N:7][C:8]=1[Cl:16])[CH3:15]

Participants

4

Reactant 2

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

Product 1

HCID 11769512Ethyl 2-chloro-4-methylnicotinate

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
50 °C

Procedure

1-Cyano-4-(N,N-dimethylamino)-1-ethoxycarbonyl-2-methyl-1,3-butadiene (25.0 g, 0.12 mol) prepared in a manner analogous to that described in Example (i) above in toluene (250 ml) was heated to 50° C. for 3 hours with stirring whereupon a steady stream of hydrogen chloride was passed through the reaction mixture. After cooling, the mixture was washed with water (250 ml). The aqueous layer was then extracted with toluene (3×100 ml). The pooled organic layers were dried with sodium sulphate and evaporated. Distillation of the residue in high vacuo yielded 2-chloro-4-methylnicotinic acid ethyl ester as colourless oil (15.3 g, 64% of theoretical yield) with b.pt.0.04 Torr 97° C.-98° C.

Workup

  1. temperatureAfter cooling
  2. washthe mixture was washed with water (250 ml)
  3. extractionThe aqueous layer was then extracted with toluene (3×100 ml)
  4. dry with materialThe pooled organic layers were dried with sodium sulphate
  5. customevaporated
  6. distillationDistillation of the residue in high vacuo
  7. customyielded

Sources & evidence

ORD record
ord-64611d51e3e7463182dde39a01bb226d
Source dataset
uspto-grants-1991_01
Patent number
US04987232

Reaction notes

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