Hydrochloric Acid → 2-Amino-6-difluoromethoxy-benzonitrile

HRID 39221

反応式

HRID 39221 の反応式
[F:1][CH:2]([F:15])[O:3][C:4]1[CH:11]=[CH:10][CH:9]=[C:8]([N+:12]([O-])=O)[C:5]=1[C:6]#[N:7].[Sn](Cl)Cl.Cl.[OH-].[Na+]>C(O)(C)C.O>[NH2:12][C:8]1[CH:9]=[CH:10][CH:11]=[C:4]([O:3][CH:2]([F:1])[F:15])[C:5]=1[C:6]#[N:7]

参加物

7

反応物 4

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 24479Stannous ChlorideHCID 581007642-Difluoromethoxy-6-nitrobenzonitrile

生成物 1

HCID 581007652-Amino-6-difluoromethoxy-benzonitrile収率 121%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 3776Isopropanol溶媒

実験手順

To a solution of 2-difluoromethoxy-6-nitro-benzonitrile (4.0 g, 14.9 mmol) (Example I3) in isopropanol (100 ml) is added tin(II) chloride (10.2 g, 53.6 mmol). Aqueous hydrochloric acid (concentrated) (14.4 ml) is added slowly and the reaction mixture is heated to reflux for 30 minutes. The reaction mixture is cooled to room temperature, diluted with water and the pH is adjusted to 10 by addition of NaOH (2M). The mixture is extracted three times with ethyl acetate. The combined organic phases are dried over sodium sulfate and concentrated to yield 2-amino-6-difluoromethoxy-benzonitrile (3.32 g, 93% yield) in pure form. 1H-NMR (CDCl3, 400 MHz): 7.05 (t, 1H), 6.65 (d, 1H), 6.55 (t, 1H), 6.50 (t, 1H), 4.25 (s, br, 2H) ppm.

後処理

  1. temperaturethe reaction mixture is heated
  2. temperatureto reflux for 30 minutes
  3. extractionThe mixture is extracted three times with ethyl acetate
  4. dry with materialThe combined organic phases are dried over sodium sulfate
  5. concentrationconcentrated

出典と根拠

ORDレコード
ord-17568dea09934574afe97a0723533b5e
出典データセット
uspto-grants-2013_09
特許番号
US08524896B2

関連ノート

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