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

HRID 613056Notes

Reaction equation

HRID 613056 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](=O)[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1.[C:29]([BH3-])#[N:30].[Na+]>CN(C)C=O>[C:22]1([CH2:21][N:30]([CH2:29][C:18]2[CH:17]=[CH:7][CH:8]=[CH:3][CH:4]=2)[C:3]2[C:4](=[O:16])[O:5][C:6]([C:10]3[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=3)=[CH:7][C:8]=2[OH:9])[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 240BenzaldehydeHCID 5003444Sodium cyanoborohydrideHCID 546812893-amino-4-hydroxy-6-phenyl-2H-pyran-2-one hydrochloride

Product 1

HCID 546813263-[Bis(phenylmethyl)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 (0.150 g, 0.626 mmol), 1% acetic acid in dimethylformamide (7 mL), benzaldehyde (0.133 mL, 1.33 mmol), sodium cyanoborohydride (0.083 g, 1.31 mmol). m.p. 130-135° C.; 1H NMR (400 MHz, DMSO-d6) δ4.26 (s, 4 H), 6.44 (s, 1 H), 7.24 (m, 6 H), 7.44 (m, 7 H), 7.69 (m, 2 H).

Sources & evidence

ORD record
ord-5d0508e0336141fd8329feedeb3dbb50
Source dataset
uspto-grants-1999_12
Patent number
US06005103

Reaction notes

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