Potassium Carbonate → 5-Methyl-3-(4-aminophenoxymethyl)isoxazole

HRID 2408364Notes

Reaction equation

HRID 2408364 reaction equation
[CH3:1][C:2]1[O:6][N:5]=[C:4]([CH2:7][O:8][C:9]2[CH:14]=[CH:13][C:12]([N+:15]([O-])=O)=[CH:11][CH:10]=2)[CH:3]=1.S(S([O-])=O)([O-])=O.[Na+].[Na+].C([O-])([O-])=O.[K+].[K+]>CO.C(Cl)Cl>[CH3:1][C:2]1[O:6][N:5]=[C:4]([CH2:7][O:8][C:9]2[CH:14]=[CH:13][C:12]([NH2:15])=[CH:11][CH:10]=2)[CH:3]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 24489Sodium DithioniteHCID 605945865-Methyl-3-(4-nitrophenoxymethyl)isoxazole

Product 1

HCID 610283115-Methyl-3-(4-aminophenoxymethyl)isoxazoleYield 46%

Reagents, catalysts & solvents 1

HCID 21226129Dichloromethane methanolSolvent

Procedure

The 5-methyl-3-(4-nitrophenoxymethyl)isoxazole (3, X═H) (2.59 g, 11.07 mmol) was dissolved in MeOH:CH2Cl2 (1:1, 600 mL). An aqueous solution of (77 mL) sodium hydrosulfite (11.93 g, 68.5 mmol) and K2CO3 (9.55 g, 69 mmol) was added dropwise under nitrogen for 30 min. The reaction was allowed to stir at room temperature for 2 h, and the organic solvents were removed under reduced pressure, diluted with water (200 mL), extracted with CH2Cl2 (3×300 mL), dried over anhydrous Na2SO4 and solvent was removed under reduced pressure. The resulting product was finally dried under high vacuum to afford 1.03 g (46%) of the 5-methyl-3-(4-aminophenoxymethyl)isoxazole (4, X═H). 1H NMR (CDCl3): δ 6.78 (d, 2H, J=8.7 Hz), 6.61 (d, 2H, J=8.4 Hz), 6.07 (s, 1H), 5.01 (s, 2H), 3.44 (s, 2H), 2.40 (s, 3H); LCMS (m/z): 205 (MH+).

Workup

  1. customthe organic solvents were removed under reduced pressure
  2. additiondiluted with water (200 mL)
  3. extractionextracted with CH2Cl2 (3×300 mL)
  4. dry with materialdried over anhydrous Na2SO4 and solvent
  5. customwas removed under reduced pressure
  6. customThe resulting product was finally dried under high vacuum

Sources & evidence

ORD record
ord-ce90600124af4b71baeeb03280a6fad3
Source dataset
uspto-grants-2014_08
Patent number
US08815848B2

Reaction notes

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