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

HRID 39221

반응식

HRID 39221 반응식
[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]

참가 물질

7

반응물 4

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

생성물 1

HCID 581007652-Amino-6-difluoromethoxy-benzonitrile수율 121%

시약·촉매·용매 2

HCID 962Water용매HCID 3776Isopropanol용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-17568dea09934574afe97a0723533b5e
출처 데이터셋
uspto-grants-2013_09
특허 번호
US08524896B2

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