3-Methoxyphenylhydrazine hydrochloride → HCID 178469355, compound

HRID 1908603Notes

Reaction equation

HRID 1908603 reaction equation
[Na].C(O[C:5](=[O:14])[C:6](=O)[CH2:7][C:8]([O:10][CH2:11][CH3:12])=[O:9])C.Cl.[CH3:16][O:17][C:18]1[CH:19]=[C:20]([NH:24][NH2:25])[CH:21]=[CH:22][CH:23]=1>C(O)(=O)C.O>[CH2:11]([O:10][C:8]([C:7]1[CH:6]=[C:5]([OH:14])[N:24]([C:20]2[CH:21]=[CH:22][CH:23]=[C:18]([O:17][CH3:16])[CH:19]=2)[N:25]=1)=[O:9])[CH3:12]

Participants

5

Reactant 2

HCID 27239403-Methoxyphenylhydrazine hydrochlorideHCID 57351814Diethyl 2-oxosuccinate,sodium salt

Product 1

HCID 178469355HCID 178469355, compound

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 962WaterSolvent

Conditions

Temperature
100 °C

Procedure

To a solution of 1.2 g of 2-Oxo-succinic acid diethyl ester monosodium salt in 10 ml acetic acid, 900 mg of (3-Methoxy-phenyl)-hydrazine hydrochloride was added and the reaction mixture was heated to 100° C. for 2 h. Then, the reaction mixture was diluted with water and extracted with ethylacetate. The organic phase was dried over MgSO4 and the solvents were removed under reduced pressure. The crude product was purified by chromatography on silica gel eluting with a gradient of n-heptane/ethyl acetate. The fractions containing the product were combined and the solvent evaporated under reduced pressure.

Workup

  1. extractionextracted with ethylacetate
  2. dry with materialThe organic phase was dried over MgSO4
  3. customthe solvents were removed under reduced pressure
  4. customThe crude product was purified by chromatography on silica gel eluting with a gradient of n-heptane/ethyl acetate
  5. additionThe fractions containing the product
  6. customthe solvent evaporated under reduced pressure

Sources & evidence

ORD record
ord-248882ee51bd4880b4a8880468cfc78e
Source dataset
uspto-grants-2013_12
Patent number
US08598179B2

Reaction notes

Loading…