1,1-Dibenzylhydrazine → 2-Amino4,5-difluorobenzoic acid, 2,2-dibenzylhydrazide

HRID 10312

Reaction equation

HRID 10312 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([NH2:12])[C:5](=[CH:9][C:10]=1[F:11])[C:6]([OH:8])=O.[CH2:13]([N:20]([CH2:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)[NH2:21])[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.Cl.C(N=C=NCCCN(C)C)C>C(Cl)Cl>[CH2:22]([N:20]([CH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)[NH:21][C:6](=[O:8])[C:5]1[CH:9]=[C:10]([F:11])[C:2]([F:1])=[CH:3][C:4]=1[NH2:12])[C:23]1[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=1

Participants

5

Reactant 3

HCID 1970501,1-DibenzylhydrazineHCID 7359652-Amino-4,5-difluorobenzoic acidHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride

Product 1

HCID 866071322-Amino4,5-difluorobenzoic acid, 2,2-dibenzylhydrazideYield 157.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
25 °C

Procedure

4,5-Difluoroanthranilic acid (4.73 g, 27.3 mmol) and N,N-dibenzylhydrazine (8.69 g, 42 mmol) are combined in 200 mL of methylene chloride. 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (EDAC) (7.85 g, 41 mmol) is then added to this solution, and the mixture is stirred for 18 hours at 25° C., The solution is washed with saturated NaHCO3, brine, and dried over magnesium sulfate. The solution is concentrated to give 15.8 g of a dark oil and purified via chromatography (SiO2, CHCl3) to give 3.4 g of the title compound as a solid. MS CI: m/z 368 (MH+).

Workup

  1. washThe solution is washed with saturated NaHCO3, brine
  2. dry with materialdried over magnesium sulfate
  3. concentrationThe solution is concentrated

Sources & evidence

ORD record
ord-7f92a3d7fb874808929e1d951998575f
Source dataset
uspto-grants-2006_08
Patent number
US07094780B1

Linked notes

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