o-Anisohydrazide → Methyl 4-{1,1-difluoro-2-[2-(2-methoxybenzoyl)hydrazino]-2-oxoethyl}benzoate

HRID 913250

Reaction equation

HRID 913250 reaction equation
[F:1][C:2]([F:16])([C:6]1[CH:11]=[CH:10][C:9]([C:12]([O:14][CH3:15])=[O:13])=[CH:8][CH:7]=1)[C:3]([OH:5])=O.[CH3:17][O:18][C:19]1[CH:28]=[CH:27][CH:26]=[CH:25][C:20]=1[C:21]([NH:23][NH2:24])=[O:22].[Cl-].C(N=C=NCCC[NH+](C)C)C>C(Cl)Cl>[F:16][C:2]([C:6]1[CH:11]=[CH:10][C:9]([C:12]([O:14][CH3:15])=[O:13])=[CH:8][CH:7]=1)([F:1])[C:3]([NH:24][NH:23][C:21](=[O:22])[C:20]1[CH:25]=[CH:26][CH:27]=[CH:28][C:19]=1[O:18][CH3:17])=[O:5]

Participants

5

Reactant 3

HCID 24051o-AnisohydrazideHCID 53519323-(Ethyliminomethylideneamino)propyl-dimethylazanium chlorideHCID 575412392-(4-(Methoxycarbonyl)phenyl)-2,2-difluoroacetic acid

Product 1

HCID 57541230Methyl 4-{1,1-difluoro-2-[2-(2-methoxybenzoyl)hydrazino]-2-oxoethyl}benzoate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of difluoro[4-(methoxycarbonyl)phenyl]acetic acid (0.12 g, 0.52 mmol) and 2-methoxybenzohydrazide (0.13 g, 0.78 mmol) in methylene chloride (2 mL) was added 3-{[(ethylimino)methylene]amino}-N,N-dimethylpropan-1-aminium chloride (0.2 g, 1.04 mmol). The resulting solution was stirred at ambient temperature for 16 hours. The reaction was purified by flash chromatography (0-4% methanol/methylene chloride) to give methyl 4-{1,1-difluoro-2-[2-(2-methoxybenzoyl)hydrazino]-2-oxoethyl}benzoate as a white solid. ESIMS calcd 379.1 (M++H), found 379.1 (M++H).

Workup

  1. customThe reaction was purified by flash chromatography (0-4% methanol/methylene chloride)

Sources & evidence

ORD record
ord-bf22575aacab48e994ccef9098e2f592
Source dataset
uspto-grants-2011_09
Patent number
US08026260B2

Linked notes

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