Acetyl chloride → Methyl 4-(hydrazinecarbonyl)benzoate

HRID 44222Notes

Reaction equation

HRID 44222 reaction equation
C(Cl)(=O)C.[CH3:5][O:6][C:7]([C:9]1[CH:25]=[CH:24][C:12]([C:13]([NH:15][NH:16]C(OC(C)(C)C)=O)=[O:14])=[CH:11][CH:10]=1)=[O:8]>CO>[NH:15]([C:13]([C:12]1[CH:24]=[CH:25][C:9]([C:7]([O:6][CH3:5])=[O:8])=[CH:10][CH:11]=1)=[O:14])[NH2:16]

Participants

4

Reactant 2

HCID 6367Acetyl chlorideHCID 12571327Tert-butyl 2-(4-(methoxycarbonyl)benzoyl)hydrazine carboxylate

Product 1

HCID 596004Methyl 4-(hydrazinecarbonyl)benzoateYield 96%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Acetyl chloride (11.8 g, 150 mmol) was added at 0° C. to methanol (200 mL) followed by the tert-butyl 2-(4-(methoxycarbonyl)benzoyl)hydrazine carboxylate (12.7 g, 43 mmol) (added as a solid). The reaction mixture was stirred at room temperature for 20 hours. The volatiles were removed in vacuo, affording methyl 4-(hydrazinecarbonyl)benzoate (8 g, 96%). The product was used without further purification. LCMS [M+H]: 195.

Workup

  1. additionadded as a solid)
  2. customThe volatiles were removed in vacuo

Sources & evidence

ORD record
ord-5ae9928ffe14410e9d67a08438ed8115
Source dataset
uspto-grants-2013_09
Patent number
US08541407B2

Reaction notes

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