Hydrochloric Acid → 4-(3,5-Dimethyl-isoxazol-4-yl)-phenylamine

HRID 450091Notes

Reaction equation

HRID 450091 reaction equation
[CH3:1][C:2]1[C:6]([C:7]2[CH:12]=[CH:11][C:10]([N+:13]([O-])=O)=[CH:9][CH:8]=2)=[C:5]([CH3:16])[O:4][N:3]=1.[Sn].Cl>C(O)C>[CH3:1][C:2]1[C:6]([C:7]2[CH:12]=[CH:11][C:10]([NH2:13])=[CH:9][CH:8]=2)=[C:5]([CH3:16])[O:4][N:3]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 5352426Tin atomHCID 153732593,5-Dimethyl-4-(4-nitrophenyl)-isoxazole

Product 1

HCID 566870724-(3,5-Dimethyl-isoxazol-4-yl)-phenylamineYield 96.6%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 3,5-dimethyl-4-(4-nitrophenyl)-isoxazole (50 mg, 0.22 mmol) in ethanol (10 ml) was added tin (52 mg, 0.44 mmol), followed by dropwise addition of concentrated hydrochloric acid (1 ml) and the reaction was stirred at room temperature for 2 hr. The reaction mixture was filtered and the filtrate evaporated to dryness. The resultant residue was diluted with water, basified with saturated bicarbonate solution, then extracted with ethyl acetate. The organic layer was washed with water, dried and concentrated to dryness to yield 4-(3,5-dimethyl-isoxazol-4-yl)-phenylamine (40 mg, 90%) as solid.

Workup

  1. filtrationThe reaction mixture was filtered
  2. customthe filtrate evaporated to dryness
  3. additionThe resultant residue was diluted with water
  4. extractionextracted with ethyl acetate
  5. washThe organic layer was washed with water
  6. customdried
  7. concentrationconcentrated to dryness

Sources & evidence

ORD record
ord-15e9e7c684f246d4beda0fcaec70d42a
Source dataset
uspto-grants-2013_07
Patent number
US08486962B2

Reaction notes

Loading…