Hydrochloric Acid → 3,7-Dimethylbenzo[d]isoxazol-5-amine

HRID 873884Notes

Reaction equation

HRID 873884 reaction equation
[CH3:1][C:2]1[C:6]2[CH:7]=[C:8]([N+:12]([O-])=O)[CH:9]=[C:10]([CH3:11])[C:5]=2[O:4][N:3]=1.O.O.Cl[Sn]Cl.Cl.[OH-].[Na+]>C(O)(=O)C>[CH3:1][C:2]1[C:6]2[CH:7]=[C:8]([NH2:12])[CH:9]=[C:10]([CH3:11])[C:5]=2[O:4][N:3]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 61436Stannous chloride dihydrateHCID 155612543,7-Dimethyl-5-nitrobenzo[d]isoxazole

Product 1

HCID 1171101573,7-Dimethylbenzo[d]isoxazol-5-amineYield 59%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

To a suspension of 3,7-dimethyl-5-nitrobenzo[d]isoxazole (Step 46.5) (50 mg, 0.260 mmol) in acetic acid (1.5 mL) was added dropwise a solution of SnCl2.2H2O (176 mg, 0.781 mmol) in HCl conc (0.316 mL, 10.41 mmol) and the resulting mixture was stirred at RT overnight. The reaction was poured into a cold 4N NaOH solution and extracted with EtOAc. The combined organic layers were dried over MgSO4, filtered and concentrated under reduced pressure. The crude product was purified by silica gel column chromatography (hexane/EtOAc 0-55%) to afford the title product (25 mg, 0.153 mmol, 59% yield) as beige solid. tR: 0.57 min (LC-MS 2); ESI-MS: 163 [M+H]+; Rf=0.23 (hexane/EtOAc 1:1).

Workup

  1. extractionextracted with EtOAc
  2. dry with materialThe combined organic layers were dried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure
  5. customThe crude product was purified by silica gel column chromatography (hexane/EtOAc 0-55%)

Sources & evidence

ORD record
ord-4e0dce44dd124f30b5c7959bf97fb874
Source dataset
uspto-grants-2015_03
Patent number
US08975417B2

Reaction notes

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