Sodium hydride → N-(4-Hydroxy-2-oxo-6-phenyl-2H-pyran-3-yl)-2-naphthalenecarboxamide

HRID 613081Notes

Reaction equation

HRID 613081 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+].[CH:19]1[C:28]2[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=2)[CH:22]=[CH:21][C:20]=1[C:29](Cl)=[O:30]>C1COCC1>[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:29]([C:20]1[CH:21]=[CH:22][C:23]2[C:28](=[CH:27][CH:26]=[CH:25][CH:24]=2)[CH:19]=1)=[O:30]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 752462-Naphthoyl chlorideHCID 546812893-amino-4-hydroxy-6-phenyl-2H-pyran-2-one hydrochloride

Product 1

HCID 54681311N-(4-Hydroxy-2-oxo-6-phenyl-2H-pyran-3-yl)-2-naphthalenecarboxamide

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

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), 2-naphthoyl chloride (0.131 g, 0.688 mmol). m.p. dec. 219° C.; 1H NMR (250 MHz, DMSO-d6) δ6.92 (s, 1 H), 7.61 (m, 5 H), 7.97 (m, 6 H), 8.62 (s, 1 H), 9.61 (s, 1 H).

Workup

  1. custom219° C.

Sources & evidence

ORD record
ord-b3ab2c53d9f3431f8d5e6f7bd0033516
Source dataset
uspto-grants-1999_12
Patent number
US06005103

Reaction notes

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