4-methyl-3-oxo-N-phenylpentanamide → HCID 178439448, compound

HRID 2368692Notes

Reaction equation

HRID 2368692 reaction equation
[CH3:1][CH:2]([CH3:15])[C:3](=O)[CH2:4][C:5]([NH:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)=[O:6]>OS(O)(=O)=O>[CH:2]([C:3]1[C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[N:7]=[C:5]([OH:6])[CH:4]=1)([CH3:15])[CH3:1]

Participants

3

Reactant 1

HCID 102198994-methyl-3-oxo-N-phenylpentanamide

Product 1

HCID 178439448HCID 178439448, compoundYield 57.8%

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Procedure

A solution of 4-methyl-3-oxo-N-phenylpentanamide (3.70 g, 18.03 mmol) in 15 mL H2SO4 was reacted as outlined in Scheme 2 above to give 1.95 g (57%) of the desired title compound. Spectroscopic data: 1H NMR (300 MHz, CDCl3) δ ppm 1.36 (d, J=6.74 Hz, 6 H) 3.45 (quin, J=6.81 Hz, 1 H) 6.67 (s, 1 H) 7.15-7.32 (m, 1 H) 7.40-7.61 (m, 2 H) 7.79 (d, J=8.50 Hz, 1 H) 12.28 (br. s., 1 H).

Sources & evidence

ORD record
ord-f72509cb49334bc98481255ef8f24c23
Source dataset
uspto-grants-2014_04
Patent number
US08703797B2

Reaction notes

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