Sodium dithionite hydrate → 3-Amino-5-(2-chlorophenyl)-4-cyanoanisole

HRID 1871482노트

반응식

HRID 1871482 반응식
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[C:9]([C:19]#[N:20])=[C:10]([N+:16]([O-])=O)[CH:11]=[C:12]([O:14][CH3:15])[CH:13]=1.O.S(S([O-])=O)([O-])=O.[Na+].[Na+]>CN(C=O)C.O>[NH2:16][C:10]1[CH:11]=[C:12]([O:14][CH3:15])[CH:13]=[C:8]([C:3]2[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=2[Cl:1])[C:9]=1[C:19]#[N:20]

참가 물질

5

반응물 2

HCID 22707037Sodium dithionite hydrateHCID 227070565-(2-Chlorophenyl)-4-cyano-3-nitroanisole

생성물 1

HCID 227070153-Amino-5-(2-chlorophenyl)-4-cyanoanisole수율 74%

시약·촉매·용매 2

HCID 962Water용매HCID 6228Dimethylformamide용매

실험 절차

The product of step (a) (300 mg, 1.0 mmol) was dissolved in DMF (3 ml) and a solution of sodium dithionite hydrate added (500 mg, 2.9 mmol in 6 ml of H2O). The solution became warm and some solid precipitated out of solution. After stirring for 30 min at room temperature, 15 ml of H2O and 2N HCl were added. This mixture was extracted with EtOAc (2×30 ml), neutralised using 2N NaOH and re-extracted with EtOAc (2×30 ml). The combined EtOAc extracts were dried over MgSO4 and the solvent removed to give the crude product. This was purified on silica gel, eluting with CH2Cl2 /MeOH (98/2, v/v) to give the subtitle compound as colourless gum (190 mg, 74%). Rf 0.29 (hexane/ether 1/1, v/v). MS m/e 276 and 278 (MNH4+).

후처리

  1. temperatureThe solution became warm
  2. customsome solid precipitated out of solution
  3. addition15 ml of H2O and 2N HCl were added
  4. extractionThis mixture was extracted with EtOAc (2×30 ml)
  5. extractionre-extracted with EtOAc (2×30 ml)
  6. dry with materialThe combined EtOAc extracts were dried over MgSO4
  7. customthe solvent removed
  8. customto give the crude product
  9. customThis was purified on silica gel
  10. washeluting with CH2Cl2 /MeOH (98/2

출처 및 근거

ORD 기록
ord-d5f5042a9da5433a93f38b342364a64b
출처 데이터셋
uspto-grants-2000_08
특허 번호
US06103738

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