2-Ketobutyric acid methyl ester → HCID 90036030, compound

HRID 925639Notes

Reaction equation

HRID 925639 reaction equation
[Br:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[NH:9][NH2:10].O=[C:12]([CH2:17][CH3:18])[C:13]([O:15][CH3:16])=[O:14]>C(O)C>[CH3:16][O:15][C:13](=[O:14])/[C:12](=[N:10]\[NH:9][C:3]1[CH:4]=[CH:5][C:6]([Cl:8])=[CH:7][C:2]=1[Br:1])/[CH2:17][CH3:18]

Participants

4

Reactant 2

HCID 5451272-Ketobutyric acid methyl esterHCID 3296360299165-75-6

Product 1

HCID 90036030HCID 90036030, compoundYield 94%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

A stirred solution of (2-bromo-4-chloro-phenyl)-hydrazine (step A) (1.98 g, 8.94 mmol) in ethanol (6.5 ml) was cooled to 0° C. and a solution of commercially available methyl 2-ketobutyrate (1.08 g, 1.04 ml, 9.3 mmol) in ethanol (2 ml) was added drop wise at 0° C. for 15 min. After the mixture was allowed to stir at room temperature for 3 h it was evaporated. The crude material (3.01 g) was purified by flash chromatography on silica gel (heptane/ethyl acetate 0-20%) to yield (Z)-2-[(2-bromo-4-chloro-phenyl)-hydrazono]-butyric acid methyl ester (2.67 g, 94%) as a light yellow solid, MS (ISP) m/z=321.3 [(M+H)+], mp 67° C.

Workup

  1. customwas evaporated
  2. customThe crude material (3.01 g) was purified by flash chromatography on silica gel (heptane/ethyl acetate 0-20%)

Sources & evidence

ORD record
ord-0361201251b3427cbc5cef12bf8b615c
Source dataset
uspto-grants-2016_03
Patent number
US09284321B2

Reaction notes

Loading…