Ammonium Chloride → 5-[2,4-Bis(benzyloxy)-6-(4-aminophenoxy)phenyl]-N-ethylisoxazole-3-carboxamide

HRID 880366Notes

Reaction equation

[CH2:1]([O:8][C:9]1[CH:14]=[C:13]([O:15][CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[CH:12]=[C:11]([O:23][C:24]2[CH:29]=[CH:28][C:27]([N+:30]([O-])=O)=[CH:26][CH:25]=2)[C:10]=1[C:33]1[O:37][N:36]=[C:35]([C:38]([NH:40][CH2:41][CH3:42])=[O:39])[CH:34]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Cl-].[NH4+]>O1CCOCC1.O.[Zn]>[CH2:1]([O:8][C:9]1[CH:14]=[C:13]([O:15][CH2:16][C:17]2[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=2)[CH:12]=[C:11]([O:23][C:24]2[CH:29]=[CH:28][C:27]([NH2:30])=[CH:26][CH:25]=2)[C:10]=1[C:33]1[O:37][N:36]=[C:35]([C:38]([NH:40][CH2:41][CH3:42])=[O:39])[CH:34]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

Conditions

Temperature: 100 °C

Procedure

To a stirred solution of 5-[2,4-bis(benzyloxy)-6-(4-nitrophenoxy)phenyl]-N-ethylisoxazole-3-carboxamide (1.45 g, 2.6 mmol) and ammonium chloride (1.4 g, 6.4 mmol, 10 eq.) in dioxane (18 mL) and water (3 mL) was added powered Zn (0.7 g, 10 mmol, 4 eq.). After heating at 100° C. for 2 hours, the solution was filtered and the filtrate was diluted with ethyl acetate and washed with 1 M NaHCO3 solution. After drying, the solvent was removed and the residue was chromatographed on silica gel eluting with hexane/ethyl acetate 3/1, to provide the title compound (0.69 g, 49% yield).

Workup

filtrationthe solution was filtered
additionthe filtrate was diluted with ethyl acetate
washwashed with 1 M NaHCO3 solution
customAfter drying
customthe solvent was removed
customthe residue was chromatographed on silica gel eluting with hexane/ethyl acetate 3/1

Sources & evidence

ORD record: ord-b06974852c574f5f831388dc18e6f704
Source dataset: uspto-grants-2015_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08993556B2

Reaction notes

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