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

HRID 613046Notes

Reaction equation

HRID 613046 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].C(O)(=O)C.[CH:21](=O)[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1.C([BH3-])#N.[Na+]>CN(C)C=O>[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][CH2:21][C:22]1[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 546812424-Hydroxy-6-phenyl-3-[(phenylmethyl)amino]-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 (0.500 g, 2.08 mmol), 1% acetic acid in dimethylformamide (20 mL), benzaldehyde (0.233 mL, 2.29 mmol), sodium cyanoborohydride (0.144 g, 2.29 mmol). m.p. dec. 205° C., 1H NMR (250 MHZ, DMSO-d6) δ4.37 (s, 2 H), 6.56 (s, 1 H), 7.27 (m, 5 H), 7.45 (m, 3 H), 7.67 (m, 2 H).

Workup

  1. custom205° C., 1H NMR (250 MHZ, DMSO-d6) δ4.37 (s, 2 H), 6.56 (s, 1 H), 7.27 (m, 5 H), 7.45 (m, 3 H), 7.67 (m, 2 H)

Sources & evidence

ORD record
ord-3e3200092d854ecaa95dcfc5772ea022
Source dataset
uspto-grants-1999_12
Patent number
US06005103

Reaction notes

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