Hydrazine hydrate (1:1) → Methyl 2-acetamino-4-hydrazinocarbonylbenzoate

HRID 2103810Notes

Reaction equation

HRID 2103810 reaction equation
O[N:2]1C2C=CC=CC=2N=[N:3]1.Cl.CN(C)CCCN=C=NCC.[NH:23]([C:27]1[CH:28]=[C:29]([CH:33]=[CH:34][C:35]=1[C:36]([O:38][CH3:39])=[O:37])[C:30](O)=[O:31])[C:24]([CH3:26])=[O:25].O.NN>CN(C)C=O>[NH:23]([C:27]1[CH:28]=[C:29]([C:30]([NH:2][NH2:3])=[O:31])[CH:33]=[CH:34][C:35]=1[C:36]([O:38][CH3:39])=[O:37])[C:24]([CH3:26])=[O:25]

Participants

6

Reactant 4

HCID 24654Hydrazine hydrate (1:1)HCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 670502013-Acetamino-4-methoxycarbonylbenzoic acid

Product 1

HCID 67050072Methyl 2-acetamino-4-hydrazinocarbonylbenzoateYield 80%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

1-Hydroxybenzotriazole (HOBt) (270 mg, 2 mmol) and 1-(3-(dimethylamino)propyl)-3-ethylcarbodiimide hydrochloride (WSC) (498 mg, 2.6 mmol) were added to a solution of 3-acetamino-4-methoxycarbonylbenzoic acid (474 mg, 2 mmol) in dimethylformamide (10 mL), and the mixture was stirred at room temperature for 3 hours. Hydrazine monohydrate (485 μL, 10 mmol) was further added at 0° C., and the mixture was stirred overnight at room temperature. The precipitated solid was filtered, and then washed with water to obtain 400 mg of the desired product as a white solid (yield 80%).

Workup

  1. stirringthe mixture was stirred overnight at room temperature
  2. filtrationThe precipitated solid was filtered
  3. washwashed with water

Sources & evidence

ORD record
ord-0ff4e90aa51244e386aee7453c0b4e7d
Source dataset
uspto-grants-2009_08
Patent number
US07576115B2

Reaction notes

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