Hydrazinium chloride → HCID 178497541, compound

HRID 2307369Notes

Reaction equation

HRID 2307369 reaction equation
[Cl:1][C:2]1[CH:11]=[C:10]([C:12](=O)[CH:13]=[CH:14][N:15](C)C)[CH:9]=[CH:8][C:3]=1[C:4]([O:6][CH3:7])=[O:5].Cl.[NH2:20]N>C(O)C>[Cl:1][C:2]1[CH:11]=[C:10]([C:12]2[CH:13]=[CH:14][NH:15][N:20]=2)[CH:9]=[CH:8][C:3]=1[C:4]([O:6][CH3:7])=[O:5]

Participants

4

Reactant 2

HCID 115031Hydrazinium chlorideHCID 85040066HCID 85040066, compound

Product 1

HCID 178497541HCID 178497541, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
77.5 °C

Procedure

To a suspension of 2-chloro-4-(3-dimethylamino-2-propen-1-on-1-yl)-benzoic acid, methyl ester (13.67g) in ethanol (53 ml) was added hydrazine monohydrochloride (7.0 g). The mixture was heated in an oil bath at 75-80° C. for one hour. The solvent was removed in vacuo. The resulting residue was dissolved in ethyl acetate, washed with water and brine, dried over anhydrous sodium sulfate, and the solvent removed in vacuo to yield the title compound as a crude solid (12 g). A purified sample had a melting point of 130-131° C.

Workup

  1. customThe solvent was removed in vacuo
  2. dissolutionThe resulting residue was dissolved in ethyl acetate
  3. washwashed with water and brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. customthe solvent removed in vacuo

Sources & evidence

ORD record
ord-8e6cc89d9a9b4b58b9a6a4a86263c33c
Source dataset
uspto-grants-2004_12
Patent number
US06831079B1

Reaction notes

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