Hydrochloric Acid → HCID 66906323, compound

HRID 2261738Notes

Reaction equation

HRID 2261738 reaction equation
[CH2:1]([O:3][C:4](=[O:15])[C:5](=O)[C:6]([CH:11]1[CH2:13][CH2:12]1)=[CH:7][N:8](C)C)[CH3:2].Cl.[Cl:17][C:18]1[CH:23]=[CH:22][CH:21]=[C:20]([Cl:24])[C:19]=1[NH:25]N.Cl>C(O)C>[CH2:1]([O:3][C:4]([C:5]1[N:25]([C:19]2[C:18]([Cl:17])=[CH:23][CH:22]=[CH:21][C:20]=2[Cl:24])[N:8]=[CH:7][C:6]=1[CH:11]1[CH2:13][CH2:12]1)=[O:15])[CH3:2]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 2723909(2,6-Dichlorophenyl)hydrazine monohydrochlorideHCID 66906104HCID 66906104, compound

Product 1

HCID 66906323HCID 66906323, compoundYield 37.8%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 3-Cycloproply-4-dimethylamino-2-oxo-but-3-enoic acid ethyl ester (6.5 mmol, 1.4 g) in ethanol (25 mL) is added 2,6-dichlorophenyl hydrazine hydrochloride (7.2 mmol, 1.5 g) followed by concentrated HCl (100 μL). The reaction is stirred for 4 h at room temperature followed by heating at 85° C. for 18 h. The reaction mixture is adsorbed onto silica gel and purified using a gradient of 0-20% EtOAc/Hexanes to yield the title compound (0.8 g, 34%). LC-ES/MS m/e 325.0 (M+1).

Workup

  1. temperatureby heating at 85° C. for 18 h
  2. custompurified

Sources & evidence

ORD record
ord-1b576d8433164ecaa83bf3050843593f
Source dataset
uspto-grants-2010_12
Patent number
US07846960B2

Reaction notes

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