1,2-Dimethylhydrazine → HCID 54498128, compound

HRID 1979137Notes

Reaction equation

HRID 1979137 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[CH:12][C:11]([C:14](=O)[CH2:15][CH2:16][C:17]([OH:19])=[O:18])=[CH:10][CH:9]=2)=[CH:4][CH:3]=1.C[NH:22][NH:23][CH3:24].[CH2:25](Cl)Cl>C(O)C>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[CH:12][C:11]([C:14](=[N:22][N:23]([CH3:24])[CH3:25])[CH2:15][CH2:16][C:17]([OH:19])=[O:18])=[CH:10][CH:9]=2)=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 13221,2-DimethylhydrazineHCID 6344DichloromethaneHCID 14116665HCID 14116665, compound

Product 1

HCID 54498128HCID 54498128, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A stirred suspension of 4-(4′-chloro-biphenyl-4-yl)-4-oxo-butyric acid (0.578 g, 0.00200 mol) in a solution of dimethylhydrazine (0.46 mL, 0.0061 mol) in absolute ethanol (6 mL) was refluxed under nitrogen for 2.4 hours and allowed to cool. The volatiles were rotary evaporated, and the residue dissolved (CH2Cl2) and purified by column chromatography on silica gel, eluting with dichloromethane-methanol (24:1) to give 0.33 g of 4-(4′-chloro-biphenyl-4-yl)-4-(dimethylhydrazono)-butyric acid as a yellow solid; mp 158-160° C.

Workup

  1. temperaturewas refluxed under nitrogen for 2.4 hours
  2. temperatureto cool
  3. custompurified by column chromatography on silica gel
  4. washeluting with dichloromethane-methanol (24:1)

Sources & evidence

ORD record
ord-6842910a440c4e7c96e8e152b1c538fd
Source dataset
uspto-grants-2001_05
Patent number
US06239288B1

Reaction notes

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