Acetic Acid → 3-[Bis(2-naphthalenylmethyl)amino]-4-hydroxy-6-phenyl-2H-pyran-2-one

HRID 613079Notes

Reaction equation

HRID 613079 reaction equation
Cl.N[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].[C:17](O)(=O)[CH3:18].[CH:21]1[C:30]2[C:25](=[CH:26][CH:27]=[CH:28][CH:29]=2)[CH:24]=[CH:23][C:22]=1[CH:31]=O.[C:33]([BH3-])#[N:34].[Na+]>CN(C)C=O>[CH:21]1[C:30]2[C:25](=[CH:26][CH:27]=[CH:28][CH:29]=2)[CH:24]=[CH:23][C:22]=1[CH2:31][N:34]([CH2:33][C:18]1[CH:17]=[CH:29][C:30]2[C:25](=[CH:24][CH:23]=[CH:22][CH:21]=2)[CH:26]=1)[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]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 62012-NaphthalenecarboxaldehydeHCID 5003444Sodium cyanoborohydrideHCID 546812893-amino-4-hydroxy-6-phenyl-2H-pyran-2-one hydrochloride

Product 1

HCID 546814823-[Bis(2-naphthalenylmethyl)amino]-4-hydroxy-6-phenyl-2H-pyran-2-one

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

The title compound was prepared by Method D using 3-amino-4-hydroxy-6-phenyl-2H-pyran-2-one hydrochloride (0.250 g, 1.04 mmol), 1% acetic acid in dimethylformamide (10 mL), 2-naphthaldehyde (0.407 g, 2.60 mmol), sodium cyanoborohydride (0.164 g, 2.60 mmol). m.p. dec. 209; 1H NMR (250 MHz, DMSO-d6) δ4.46 (s, 4 H), 6.38 (s, 1 H), 7.44 (m, 8H), 7.77 (m, 13H).

Sources & evidence

ORD record
ord-12135f71cc694e449b02c827e141c7e0
Source dataset
uspto-grants-1999_12
Patent number
US06005103

Reaction notes

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