(3-Chloropropyl)benzene → N-(4-Hydroxy-2-oxo-6-phenyl-2H-pyran-3-yl)benzenepropanamide

HRID 2394005Notes

Reaction equation

HRID 2394005 reaction equation
Cl.[NH2:2][C:3]1[C:4](=[O:16])[O:5][C:6]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)=[CH:7][C:8]=1[OH:9].[H-].[Na+].[CH2:19](Cl)[CH2:20][CH2:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1.C1C[O:32]CC1>>[OH:9][C:8]1[CH:7]=[C:6]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[O:5][C:4](=[O:16])[C:3]=1[NH:2][C:19](=[O:32])[CH2:20][CH2:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1

Participants

5

Reactant 4

HCID 7706(3-Chloropropyl)benzeneHCID 8028TetrahydrofuranHCID 24758Sodium hydrideHCID 546812893-amino-4-hydroxy-6-phenyl-2H-pyran-2-one hydrochloride

Product 1

HCID 54681304N-(4-Hydroxy-2-oxo-6-phenyl-2H-pyran-3-yl)benzenepropanamide

Procedure

The title compound was prepared by Method E using 3-amino-4-hydroxy-6-phenyl-2H-pyran-2-one hydrochloride (0.150 g, 0.626 mmol), THF (6 mL), 60% sodium hydride (0.028 mL, 0.688 mmol), hydrocinnamyl chloride (0.131 g, 0.688 mmol). m.p. 191°-193° C.; 1H NMR (250 MHz, DMSO-d6) δ 2.65 (t, 2 H), 2.89 (t, 2 H), 6.86 (s, 1 H), 7.26 (m, 5 H), 7.53 (m, 3 H), 7.84 (m, 2 H), 9.28 (s, 1 H).

Sources & evidence

ORD record
ord-e6f3d0934260473d8c33fd2d3f016930
Source dataset
uspto-grants-1998_09
Patent number
US05808062

Reaction notes

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