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

HRID 1871482ノート

反応式

HRID 1871482 の反応式
[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]

参加物

5

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6228Dimethylformamide溶媒

実験手順

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+).

後処理

  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

出典と根拠

ORDレコード
ord-d5f5042a9da5433a93f38b342364a64b
出典データセット
uspto-grants-2000_08
特許番号
US06103738

反応ノート

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