Hydrochloric Acid → HCID 10061987, compound

HRID 1087182Notes

Reaction equation

HRID 1087182 reaction equation
[CH3:1][N:2]([C:11]1[CH:12]=[C:13]([C:20]2([CH3:25])OCC[O:21]2)[CH:14]=[CH:15][C:16]=1[N+:17]([O-])=O)[C:3]1[CH:8]=[CH:7][C:6]([F:9])=[CH:5][C:4]=1[F:10].Cl>CC(C)=O>[NH2:17][C:16]1[CH:15]=[CH:14][C:13]([C:20](=[O:21])[CH3:25])=[CH:12][C:11]=1[N:2]([CH3:1])[C:3]1[CH:8]=[CH:7][C:6]([F:9])=[CH:5][C:4]=1[F:10]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 19817746HCID 19817746, compound

Product 1

HCID 10061987HCID 10061987, compoundYield 21.1%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A solution of 2-{3-[N-methyl-N-(2,4-difluorophenyl)amino]-4-nitrophenyl}-2-methyl-1,3-dioxolane (6.6 g) and 3N-hydrochloric acid (60 ml) in acetone (120 ml) was stirred at room temperature overnight and evaporated. The residue was dissolved in ethyl acetate, washed with water and an aqueous solution of sodium bicarbonate, and concentrated to dryness. A mixture of the residual oil (5.3 g), iron powder (5 g) and ammonium chloride (0.5 g) in ethanol (120 ml) and water (60 ml) was stirred and refluxed for 1 hour. The mixture was filtered and the filtrate was evaporated. The residue was purified by column chromatography on silica gel eluting with a mixture of toluene and ethyl acetate (20:1) to give crystals of 4'-amino-3'-[N-methyl-N-(2,4-difluorophenyl)amino]acetophenone (1.1 g).

Workup

  1. customevaporated
  2. dissolutionThe residue was dissolved in ethyl acetate
  3. washwashed with water
  4. concentrationan aqueous solution of sodium bicarbonate, and concentrated to dryness
  5. additionA mixture of the residual oil (5.3 g), iron powder (5 g) and ammonium chloride (0.5 g) in ethanol (120 ml) and water (60 ml)
  6. temperaturerefluxed for 1 hour
  7. filtrationThe mixture was filtered
  8. customthe filtrate was evaporated
  9. customThe residue was purified by column chromatography on silica gel eluting with a mixture of toluene and ethyl acetate (20:1)

Sources & evidence

ORD record
ord-76aae9ef7d8949d18f22b77eccbfaffa
Source dataset
uspto-grants-1991_07
Patent number
US05034417

Reaction notes

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