Dimethylformamide → 6-Chloro-5-nitro-1H-isochromen-1-one

HRID 418475ノート

反応式

HRID 418475 の反応式
[Cl:1][C:2]1[CH:11]=[CH:10][C:5]([C:6]([O:8][CH3:9])=[O:7])=[C:4]([CH3:12])[C:3]=1[N+:13]([O-:15])=[O:14].CN(C)C=O.COC(OC)N(C)C.C(OCC)(=O)C>>[Cl:1][C:2]1[C:3]([N+:13]([O-:15])=[O:14])=[C:4]2[C:5](=[CH:10][CH:11]=1)[C:6](=[O:7])[O:8][CH:9]=[CH:12]2

参加物

5

反応物 4

HCID 6228DimethylformamideHCID 8857Ethyl AcetateHCID 78373Dimethylformamide dimethyl acetalHCID 10657064Methyl 4-chloro-2-methyl-3-nitrobenzoate

生成物 1

HCID 595157256-Chloro-5-nitro-1H-isochromen-1-one

反応条件

温度
120 °C

実験手順

A pressure tube was charged with methyl 4-chloro-2-methyl-3-nitrobenzoate (13 g, 57 mmol), N,N-dimethylformamide (10 mL, 200 mmol) and 1,1-dimethoxy-N,N-dimethylmethanamine (26.5 mL, 200 mmol). The reaction was heated at 120° C. for 20 h. The solvents were removed and the resultant brown residue was redissolved in ethyl acetate (600 mL, 6000 mmol) and 130-270 mesh 60A silica gel (500 g, 6000 mmol) was added. The reaction was stirred with a mechanical stirrer for 8 h. The reaction was filtered, washed with ethyl acetate (400 mL). the organics were combined. and the solvents were removed under reduced pressure. The residue was purified by flash chromatography to give the desired product.

後処理

  1. customThe solvents were removed
  2. filtrationThe reaction was filtered
  3. washwashed with ethyl acetate (400 mL)
  4. customand the solvents were removed under reduced pressure
  5. customThe residue was purified by flash chromatography

出典と根拠

ORDレコード
ord-a9bb60d22b764216bc9dca607fccf882
出典データセット
uspto-grants-2012_01
特許番号
US08093265B2

反応ノート

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