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

HRID 986574
Notes
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Reaction equation

HRID 986574 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]
ParticipantsProcedureWorkupSources & evidenceReaction notes

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 887
Methanol
Solvent
HCID 962WaterSolvent2×

Procedure

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

Workup

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

Sources & evidence

ORD record
ord-295b5f9254d74ab89d22c8734320c7c9
Source dataset
uspto-grants-1987_12
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US04714492

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes