1,2-Difluoro-3-nitrobenzene → 2-fluoro-N-(4-methoxybutyl)-6-nitroaniline

HRID 1184123ノート

反応式

HRID 1184123 の反応式
[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([N+:8]([O-:10])=[O:9])[C:3]=1F.Cl.[CH3:13][O:14][CH2:15][CH2:16][CH2:17][CH2:18][NH2:19].C(N(C(C)C)CC)(C)C>C(#N)C>[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([N+:8]([O-:10])=[O:9])[C:3]=1[NH:19][CH2:18][CH2:17][CH2:16][CH2:15][O:14][CH3:13]

参加物

5

反応物 3

HCID 813351,2-Difluoro-3-nitrobenzeneHCID 81531DiisopropylethylamineHCID 457923494-Methoxybutan-1-amine hydrochloride2 回

生成物 1

HCID 583552882-fluoro-N-(4-methoxybutyl)-6-nitroaniline収率 98.2%

試薬・触媒・溶媒 1

HCID 6342Acetonitrile溶媒

反応条件

温度
60 °C

実験手順

To a solution of 1,2-difluoro-3-nitrobenzene (5.15 g) and 4-methoxybutan-1-amine hydrochloride (5.42 g) in acetonitrile (100 ml) was added diisopropylethylamine (17 μl), and the mixture was stirred at 60° C. for 12 hr. 4-Methoxybutan-1-amine hydrochloride (1.00 g) was further added, and the mixture was stirred at 70° C. for 5 hr. The reaction mixture was concentrated under reduced pressure, saturated aqueous sodium hydrogen carbonate was added, and the mixture was extracted with ethyl acetate. The extract was dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was subjected to silica gel column chromatography, and a fraction eluted with hexane-ethyl acetate-hexane (3:7) was concentrated under reduced pressure to give the object product (7.70 g).

後処理

  1. stirringthe mixture was stirred at 70° C. for 5 hr
  2. concentrationThe reaction mixture was concentrated under reduced pressure, saturated aqueous sodium hydrogen carbonate
  3. additionwas added
  4. extractionthe mixture was extracted with ethyl acetate
  5. dry with materialThe extract was dried over anhydrous magnesium sulfate
  6. concentrationconcentrated under reduced pressure
  7. washa fraction eluted with hexane-ethyl acetate-hexane (3:7)
  8. concentrationwas concentrated under reduced pressure

出典と根拠

ORDレコード
ord-a96aead8d88049138b4e05147de3f331
出典データセット
uspto-grants-2014_03
特許番号
US08664380B2

反応ノート

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