1-Naphthaleneacetic Acid → N-(4-Hydroxy-2-oxo-6-phenyl-2H-pyran-3-yl)-2-naphthaleneacetamide

HRID 613080Notes

Reaction equation

HRID 613080 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+].[C:19](Cl)(=[O:23])[C:20](Cl)=O.[C:25]1(CC(O)=O)[C:34]2[C:29](=[CH:30][CH:31]=[CH:32][CH:33]=2)[CH:28]=[CH:27][CH:26]=1>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:19](=[O:23])[CH2:20][C:27]1[CH:26]=[CH:25][C:34]2[C:29](=[CH:30][CH:31]=[CH:32][CH:33]=2)[CH:28]=1

Participants

6

Reactant 4

HCID 68621-Naphthaleneacetic AcidHCID 24758Sodium hydrideHCID 65578Oxalyl chlorideHCID 546812893-amino-4-hydroxy-6-phenyl-2H-pyran-2-one hydrochloride

Product 1

HCID 54681255N-(4-Hydroxy-2-oxo-6-phenyl-2H-pyran-3-yl)-2-naphthaleneacetamide

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 (0.200 g, 0.835 mmol), THF (9 mL), 60% sodium hydride (0.037 mL, 0.918 mmol), oxalyl chloride (0.080 mL, 0.918 mmol), 2-naphthalyl acetic acid (0.170 g, 0.918 mmol). m.p. dec. 227° C.; 1H NMR (250 MHz, DMSO-d6) δ4.17 (s, 2 H), 6.84 (s, 1 H), 7.50 (m, 6 H), 7.83 (m, 4 H), 7.93 (d, 1 H), 8.17 (d, 1 H), 9.58 (s, 1 H).

Workup

  1. custom227° C.

Sources & evidence

ORD record
ord-02a7b497766b47929b7b0ea2729ee73e
Source dataset
uspto-grants-1999_12
Patent number
US06005103

Reaction notes

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