Water → 5-chloro-2-methyl-3-nitroaniline

HRID 618256Notes

Reaction equation

HRID 618256 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([N+:12]([O-:14])=[O:13])[C:5]([CH3:11])=[C:6]([N+:8]([O-])=O)[CH:7]=1.O.S(S([O-])=O)([O-])=O.[Na+].[Na+]>CO>[Cl:1][C:2]1[CH:3]=[C:4]([N+:12]([O-:14])=[O:13])[C:5]([CH3:11])=[C:6]([NH2:8])[CH:7]=1

Participants

5

Reactant 3

HCID 962WaterHCID 24489Sodium DithioniteHCID 2749341HCID 2749341, compound

Product 1

HCID 27493455-chloro-2-methyl-3-nitroanilineYield 85.9%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

5-Chloro-2-methyl-1,3-dinitro-benzene (1.96 g, from above) was suspended in methanol (80 mL) and water (20 mL) under N2. Sodium dithionite (5.51 g) was added portionwise and the mixture was stirred at room temperature for 3 hr. The reaction mixture was filtered and washed with methanol. The filtrate was then removed under reduced pressure and the residue was partitioned between ethyl acetate (150 mL) and brine (150 mL). The organic layer was dried over magnesium sulfate and evaporated to afford 5-chloro-2-methyl-3-nitro-phenylamine (1.45 g).

Workup

  1. filtrationThe reaction mixture was filtered
  2. washwashed with methanol
  3. customThe filtrate was then removed under reduced pressure
  4. customthe residue was partitioned between ethyl acetate (150 mL) and brine (150 mL)
  5. dry with materialThe organic layer was dried over magnesium sulfate
  6. customevaporated

Sources & evidence

ORD record
ord-0e51da76bfe7483a8f559cf29374efbe
Source dataset
uspto-grants-1999_09
Patent number
US05952362

Reaction notes

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