Dimethylformamide → 2-chloro-5-(5-methyl-1H-pyrazol-3-yl)-benzoic acid methyl ester

HRID 456873ノート

反応式

HRID 456873 の反応式
[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]

参加物

5

反応物 3

HCID 6228DimethylformamideHCID 878351,1-Dimethoxyethyl(dimethyl)amineHCID 58818179Methyl 5-acetyl-2-chlorobenzoate

生成物 1

HCID 588181962-chloro-5-(5-methyl-1H-pyrazol-3-yl)-benzoic acid methyl ester

試薬・触媒・溶媒 1

HCID 31374Dimethylacetamide溶媒

実験手順

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).

後処理

  1. concentrationconcentrated in vacuo
  2. additionThe residue was diluted with ethanol (18 mL) and tetrahydrofuran (2 mL)
  3. additionHydrazine hydrate (0.34 mL) was added
  4. concentrationThe mixture was concentrated in vacuo
  5. customThe residue was purified by flash column chromatography (gradient 0–10% methanol-ethyl acetate)

出典と根拠

ORDレコード
ord-f7856af6d0ad42eb82cb6ab1c049073a
出典データセット
uspto-grants-2007_03
特許番号
US07186742B2

反応ノート

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