Hydrochloric Acid → Methyl 1-ethyl-6-methyl-2-(4'-chlorophenyl)-4-oxonicotinate

HRID 1089049Notes

Reaction equation

HRID 1089049 reaction equation
CO.[CH3:3][O:4][C:5]([C:7]1[C:12](=[O:13])[CH:11]=[C:10]([CH3:14])O[C:8]=1[C:15]1[CH:20]=[CH:19][C:18]([Cl:21])=[CH:17][CH:16]=1)=[O:6].[CH2:22]([NH2:24])[CH3:23].Cl>O.C(O)(=O)C>[CH2:22]([N:24]1[C:10]([CH3:14])=[CH:11][C:12](=[O:13])[C:7]([C:5]([O:4][CH3:3])=[O:6])=[C:8]1[C:15]1[CH:20]=[CH:19][C:18]([Cl:21])=[CH:17][CH:16]=1)[CH3:23]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 887MethanolHCID 6341EthylamineHCID 14075263HCID 14075263, compound

Product 1

HCID 14075279Methyl 1-ethyl-6-methyl-2-(4'-chlorophenyl)-4-oxonicotinate

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 962WaterSolvent

Procedure

A 1000 ml flask is fitted with a magnetic stirring bar and a sidearm addition funnel. 500 ml of methanol, 30 ml of glacial acetic acid and 60 g of 3-methoxycarbonyl-6-methyl-2-(4'-chlorophenyl)-4-pyrone are added. 120 ml of 70% aqueous ethylamine is placed in the addition tunnel and added very slowly (4 hr. addition time). 50 ml of water is then added followed by 100 ml of concentrated HCl (cooling required). The reaction mixture is allowed to stand undisturbed for 30 minutes. The bulk of the methanol is then removed in vacuo leaving 46.1 g of methyl 1-ethyl-6-methyl-2-(4'-chlorophenyl)-4-oxonicotinate. mp (methylene chloride/ether)=217°-219° C.

Workup

  1. customA 1000 ml flask is fitted with a magnetic stirring bar and a sidearm addition funnel
  2. additionadded very slowly
  3. addition(4 hr. addition time)
  4. customThe bulk of the methanol is then removed in vacuo

Sources & evidence

ORD record
ord-1ac85062229049a0815936f4610f2764
Source dataset
uspto-grants-1990_10
Patent number
US04964896

Reaction notes

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