Water → HCID 539799, compound

HRID 1626043Notes

Reaction equation

HRID 1626043 reaction equation
CN/[C:3](/[CH3:9])=[CH:4]/[C:5]([O:7][CH3:8])=[O:6].N1C=CC=CC=1.[N+:16]([C:19]1[CH:27]=[CH:26][C:22]([C:23](Cl)=[O:24])=[CH:21][CH:20]=1)([O-:18])=[O:17].[OH2:28]>C1COCC1>[N+:16]([C:19]1[CH:27]=[CH:26][C:22]([C:23]([CH:4]([C:3](=[O:28])[CH3:9])[C:5]([O:7][CH3:8])=[O:6])=[O:24])=[CH:21][CH:20]=1)([O-:18])=[O:17]

Participants

6

Reactant 4

HCID 962WaterHCID 1049PyridineHCID 85024-Nitrobenzoyl chlorideHCID 584604513412-12-9

Product 1

HCID 539799HCID 539799, compoundYield 95%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

(E)-methyl 3-(methylamino)but-2-enoate (12.9 g, 100 mmol) was dissolved in 300 mL anhydrous THF and 12 mL pyridine was added into the solution dropwise. The reaction was cooled in ice bath, and 4-nitrobenzoyl chloride (18.7 mL in 50 mL anhydrous THF) was added into the solution slowly. The reaction was warmed up to room temperature and stirred for overnight. After adding 300 mL water into the reaction, the solution was extracted by ethyl acetate for 3 times. The combined organic layer was further washed with water and brine, dried over Na2SO4, and removed under the vacuum to give methyl 2-(4-nitrobenzoyl)-3-oxobutanoate as the solid without further purification (25.2 g, 95% yield).

Workup

  1. temperatureThe reaction was cooled in ice bath
  2. custominto the reaction
  3. extractionthe solution was extracted by ethyl acetate for 3 times
  4. washThe combined organic layer was further washed with water and brine
  5. dry with materialdried over Na2SO4
  6. customremoved under the vacuum

Sources & evidence

ORD record
ord-25b6c16e91f94c338fadfd3281115101
Source dataset
uspto-grants-2014_07
Patent number
US08785442B2

Reaction notes

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