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

HRID 2107892Notes

Reaction equation

HRID 2107892 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 mls of methanol, 30 mls of glacial acetic acid and 60 gms of 3-methoxycarbonyl-6-methyl-2-(4'-chlorophenyl)-4-pyrone are added. 120 mls of 70% aqueous ethylamine is placed in the addition funnel and added very slowly (4 hr. addition time). 50 mls of water is then added followed by 100 mls 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 gms 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-d88bc6a9e6f740f9a19c12b8eee6318f
Source dataset
uspto-grants-1990_06
Patent number
US04936904

Reaction notes

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