Methyl acetoacetate → 90-31-3

HRID 1853093Notes

Reaction equation

HRID 1853093 reaction equation
Cl.[Cl:2][C:3]1[CH:4]=[C:5]([NH:9][NH2:10])[CH:6]=[CH:7][CH:8]=1.[C:11](OC)(=[O:16])[CH2:12][C:13]([CH3:15])=O>C(O)(=O)C>[Cl:2][C:3]1[CH:4]=[C:5]([N:9]2[C:11](=[O:16])[CH:12]=[C:13]([CH3:15])[NH:10]2)[CH:6]=[CH:7][CH:8]=1

Participants

4

Reactant 2

HCID 7757Methyl acetoacetateHCID 75331m-Chlorophenylhydrazine hydrochloride

Product 1

HCID 1875642090-31-3

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
60 °C

Procedure

To a solution of 3-chlorophenylhydrazine hydrochloride (CAS No. 2312-23-4) (14.2 g) in acetic acid (60 mL) was added methyl acetoacetate (10.70 mL). The reaction was allowed to stir overnight at 60° C. and the volatiles were removed under reduced pressure and partitioned between saturated sodium bicarbonate and EtOAc. The organic layer was separated and concentrated under reduced pressure and purified by silica gel column chromatography using a gradient of 0-75% EtOAc in heptanes. The resulting solid was triturated with heptanes to give the title compound (10.3 g) having the following physical data as a white solid.

Workup

  1. customthe volatiles were removed under reduced pressure
  2. custompartitioned between saturated sodium bicarbonate and EtOAc
  3. customThe organic layer was separated
  4. concentrationconcentrated under reduced pressure
  5. custompurified by silica gel column chromatography
  6. customThe resulting solid was triturated with heptanes

Sources & evidence

ORD record
ord-1af4904e0b034718a403cb440daeb3e6
Source dataset
uspto-grants-2015_02
Patent number
US08962623B2

Reaction notes

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