Sodium sulfide nonahydrate → 5-Fluoro-2-methyl-3-nitroaniline

HRID 1416905Notes

Reaction equation

HRID 1416905 reaction equation
[N+:1]([C:4]1[CH:9]=[C:8]([F:10])[CH:7]=[C:6]([N+:11]([O-])=O)[C:5]=1[CH3:14])([O-:3])=[O:2].O.O.O.O.O.O.O.O.O.[S-2].[Na+].[Na+]>C(O)C.O>[NH2:11][C:6]1[CH:7]=[C:8]([F:10])[CH:9]=[C:4]([N+:1]([O-:3])=[O:2])[C:5]=1[CH3:14]

Participants

5

Reactant 2

HCID 73972Sodium sulfide nonahydrateHCID 184653725-Fluoro-2-methyl-1,3-dinitrobenzene

Product 1

HCID 184653775-Fluoro-2-methyl-3-nitroaniline

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent2×

Procedure

A solution of 2,6-dinitro-4-fluorotoluene (8.1 g) in ethanol (130 mL) is treated dropwise with a solution of sodium sulfide nonahydrate (16.39 g) in water (90 mL). The mixture is allowed to stir at room temperature for 2.5 hours, then diluted with water (500 mL) and extracted with ethyl acetate (4×500 mL). The combined extracts are dried over sodium sulfate and rotary evaporated. The residue is purified by flash chromatography on silica gel, eluting with 15% ethyl acetate/hexanes to afford 2-amino-4-fluoro-6-nitrotoluene as a solid.

Workup

  1. extractionextracted with ethyl acetate (4×500 mL)
  2. dry with materialThe combined extracts are dried over sodium sulfate and rotary evaporated
  3. customThe residue is purified by flash chromatography on silica gel
  4. washeluting with 15% ethyl acetate/hexanes

Sources & evidence

ORD record
ord-8d1699e30dd6444e941f08c279f513ec
Source dataset
uspto-grants-1999_06
Patent number
US05916900

Reaction notes

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