Dimethylformamide → 2-chloro-5-(5-methyl-1H-pyrazol-3-yl)-benzoic acid methyl ester
Reaction equation
[CH3:1][O:2][C:3](=[O:14])[C:4]1[CH:9]=[C:8]([C:10](=O)[CH3:11])[CH:7]=[CH:6][C:5]=1[Cl:13].CO[C:17](OC)([N:19](C)C)[CH3:18].C[N:25](C)C=O>CN(C)C(=O)C>[CH3:1][O:2][C:3](=[O:14])[C:4]1[CH:9]=[C:8]([C:10]2[CH:11]=[C:17]([CH3:18])[NH:19][N:25]=2)[CH:7]=[CH:6][C:5]=1[Cl:13]Participants
5
Procedure
A solution of 5-acetyl-2-chloro-benzoic acid methyl ester (1.58 g, 7.5 mmol) and N,N-dimethylacetamide dimethylacetal in N,N-dimethylformamide and N,N-dimethylacetamide was stirred at 90° C. for 3 h. The mixture was cooled to room temperature and concentrated in vacuo. The residue was diluted with ethanol (18 mL) and tetrahydrofuran (2 mL). Hydrazine hydrate (0.34 mL) was added and the mixture was stirred at room temperature for 16 h. The mixture was concentrated in vacuo. The residue was purified by flash column chromatography (gradient 0-10% methanol-ethyl acetate) to afford the title compound (1.0 g).
Workup
- concentrationconcentrated in vacuo
- additionThe residue was diluted with ethanol (18 mL) and tetrahydrofuran (2 mL)
- additionHydrazine hydrate (0.34 mL) was added
- concentrationThe mixture was concentrated in vacuo
- customThe residue was purified by flash column chromatography (gradient 0-10% methanol-ethyl acetate)
Sources & evidence
- ORD record
- ord-b3b383b9515748fead96a2b84a27ac18
- Source dataset
- uspto-grants-2009_06
- Patent number
- US07553972B2
Reaction notes
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