Acetic Acid → Methyl 1-allyl-6-methyl-2-(4'-chlorophenyl)-4-oxonicotinate

HRID 2107897Notes

Reaction equation

HRID 2107897 reaction equation
[CH3:1][O:2][C:3]([C:5]1[C:10](=[O:11])[CH:9]=[C:8]([CH3:12])O[C:6]=1[C:13]1[CH:18]=[CH:17][C:16]([Cl:19])=[CH:15][CH:14]=1)=[O:4].C(O)(=O)C.[CH2:24]([NH2:27])[CH:25]=[CH2:26].Cl>O.CO>[CH2:24]([N:27]1[C:8]([CH3:12])=[CH:9][C:10](=[O:11])[C:5]([C:3]([O:2][CH3:1])=[O:4])=[C:6]1[C:13]1[CH:18]=[CH:17][C:16]([Cl:19])=[CH:15][CH:14]=1)[CH:25]=[CH2:26]

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 313Hydrochloric AcidHCID 7853AllylamineHCID 14075263HCID 14075263, compound

Product 1

HCID 22159875Methyl 1-allyl-6-methyl-2-(4'-chlorophenyl)-4-oxonicotinateYield 87.7%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent2×

Procedure

10 gms of 3-methoxycarbonyl-6-methyl-2-(4'-chlorophenyl)-4-pyrone, 1.65 gms glacial acetic acid and 100 mls of methanol are mixed in 500 ml flask fitted with a magnetic stirring bar and sidearm additionl funnel. 6.15 gms of allylamine are slowly added (one hour addition time). Three hours later 20 mls of water and 8 mls of concentrate HCl are added. This reaction mixture is allowed to stand at room temperature for one hour, then is poured into 400 mls of water and extracted with methylene chloride (2×100 mls). Removal of the solvent yields 10 gms of crude methyl 1-allyl-6-methyl-2-(4'-chlorophenyl)-4-oxonicotinate.

Workup

  1. customfitted with a magnetic stirring bar and sidearm additionl funnel
  2. addition(one hour addition time)
  3. extractionextracted with methylene chloride (2×100 mls)
  4. customRemoval of the solvent

Sources & evidence

ORD record
ord-816d146482e64ccc8c2158bdf5721daa
Source dataset
uspto-grants-1990_06
Patent number
US04936904

Reaction notes

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