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

HRID 1871482Notes

Reaction equation

HRID 1871482 reaction equation
[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]

Participants

5

Reactant 2

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

Product 1

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

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

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+).

Workup

  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

Sources & evidence

ORD record
ord-d5f5042a9da5433a93f38b342364a64b
Source dataset
uspto-grants-2000_08
Patent number
US06103738

Reaction notes

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