Hydrochloric Acid → HCID 76071676, compound

HRID 927045Notes

Reaction equation

HRID 927045 reaction equation
C(OC(=O)[NH:7][C:8]1[C:9]([C:13]2[CH:18]=[CH:17][C:16]([O:19][CH2:20][CH2:21][CH2:22][C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=3)=[CH:15][CH:14]=2)=[N:10][O:11][CH:12]=1)(C)(C)C.Cl.C(OCC)(=O)C>O1CCOCC1>[C:23]1([CH2:22][CH2:21][CH2:20][O:19][C:16]2[CH:17]=[CH:18][C:13]([C:9]3[C:8]([NH2:7])=[CH:12][O:11][N:10]=3)=[CH:14][CH:15]=2)[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 8857Ethyl AcetateHCID 90203479HCID 90203479, compound

Product 1

HCID 76071676HCID 76071676, compoundYield 55%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

{3-[4-(3-Phenyl-propoxy)-phenyl]-isoxazol-4-yl}-carbamic acid tert-butyl ester (54 mg, 0.137 mmol) was dissolved in dioxane (9 mL) and treated with conc. HCl (1.5 mL). After stirring for 12 h at rt the reaction mixture was quenched with 10 mL of satd aqueous NaHCO3. The organic layer was separated and dried over Na2SO4. Filtration followed by removal of volatiles under reduce d pressure gave crude product. 3-[4-(3-Phenyl-propoxy)-phenyl]-isoxazol-4-ylamine (22 mg, 55%) was isolated as a white solid by column chromatography (30% ethyl acetate in hexanes). HRMS: 295.144 (M+1).

Workup

  1. customwas quenched with 10 mL of satd aqueous NaHCO3
  2. customThe organic layer was separated
  3. dry with materialdried over Na2SO4
  4. filtrationFiltration
  5. customfollowed by removal of volatiles
  6. customgave crude product

Sources & evidence

ORD record
ord-868b08bac6724ef2a13366ac8ba3079b
Source dataset
uspto-grants-2016_03
Patent number
US09290465B2

Reaction notes

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