Bis(2,4,6-trichlorophenyl) propanedioate → HCID 118272039, compound

HRID 588086Notes

Reaction equation

HRID 588086 reaction equation
ClC1C=C(Cl)C=C(Cl)C=1[O:10][C:11](=O)[CH2:12][C:13](OC1C(Cl)=CC(Cl)=CC=1Cl)=[O:14].[NH2:26][C:27]([CH:34]([CH3:36])[CH3:35])=[CH:28][C:29]([O:31][CH2:32][CH3:33])=[O:30]>BrC1C=CC=CC=1.CCOC(C)=O.CCOCC>[OH:14][C:13]1[C:28]([C:29]([O:31][CH2:32][CH3:33])=[O:30])=[C:27]([CH:34]([CH3:35])[CH3:36])[NH:26][C:11](=[O:10])[CH:12]=1

Participants

5

Reactant 2

HCID 2783450Bis(2,4,6-trichlorophenyl) propanedioateHCID 59557418Ethyl 3-amino-4-methyl-pent-2-enoate

Product 1

HCID 118272039HCID 118272039, compound

Reagents, catalysts & solvents 2

HCID 7961BromobenzeneSolventHCID 21584169Diethylether ethylacetateSolvent

Procedure

Malonic acid bis(2,4,6-trichlorophenyl) ester (1.4 g, 3.05 mmol) and ethyl 3-amino-4-methylpent-2-enoate (480 mg, 3.05 mmol) in bromobenzene (5 mL) was heated at 155° C. for 45 min. The reaction mixture was diluted with EtOAc/Et2O then concentrated in vacuo until a solid crashed out of solution. The solid was collected and rinsed with Et2O and ethyl acetate. The filtrate was concentrated in vacuo, diluted with DCM, and purified by flash chromatography (12-100% EtOAc/isohexane). The fractions containing pure product were concentrated in vacuo and the resulting solid triturated with Et2O and combined with the first batch of solid to give ethyl 4-hydroxy-2-isopropyl-6-oxo-1,6-dihydropyridine-3-carboxylate. MS ESI calc'd. for C11H15NO4 [M+1]+ 226. found 226.

Workup

  1. concentrationthen concentrated in vacuo until a solid
  2. customThe solid was collected
  3. washrinsed with Et2O and ethyl acetate
  4. concentrationThe filtrate was concentrated in vacuo
  5. additiondiluted with DCM
  6. custompurified by flash chromatography (12-100% EtOAc/isohexane)
  7. additionThe fractions containing pure product
  8. concentrationwere concentrated in vacuo
  9. customthe resulting solid triturated with Et2O

Sources & evidence

ORD record
ord-4cd59071678f429d8b58c826df02c0af
Source dataset
uspto-grants-2016_01
Patent number
US09226922B2

Reaction notes

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