Propionic anhydride → [3-[Di(propanoyloxy)methyl]-1-methyl-2-oxo-4-quinolyl] propanoate

HRID 1769610Notes

Reaction equation

[CH3:1][N:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5]([OH:12])=[C:4]([CH:13]=[O:14])[C:3]1=[O:15].C([O:20][C:21](=[O:24])[CH2:22][CH3:23])(=O)CC>>[CH3:1][N:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5]([O:12][C:5](=[O:12])[CH2:6][CH3:7])=[C:4]([CH:13]([O:20][C:21](=[O:24])[CH2:22][CH3:23])[O:14][C:13](=[O:14])[CH2:4][CH3:3])[C:3]1=[O:15]

Participants

Reactant 2

HCID 31263Propionic anhydride

HCID 1354542351-methyl-3-formyl-4-hydroxy-2(1H)-quinolinone

Product 1

HCID 5274968[3-[Di(propanoyloxy)methyl]-1-methyl-2-oxo-4-quinolyl] propanoate

Procedure

Following the procedure of Example 5, 1-methyl-3-formyl-4-hydroxy-2(1H)-quinolinone (from Preparation B) was acylated with propanoic anhydride to give 1-methyl-3-[di-(1-oxopropoxy)]methyl-4-(1-oxopropoxy)-2(1H)-quinolinone. That the expected product was obtained was confirmed by the spectral data: MS (CI): m/e 390 (M.+ +1); NMR (CDCl3): δ1.14 (t, 6H, 2 x CH3CH2), 1.38 (t, 3H, CH3CH2), 2.39 (m, 4H, 2 x CH2CO), 2.83 (q, 2H, CH3CH2CO), 3.74 (s, 3H, NCH3), 8.10 (s, 1 H, (CH3CH2COO)2CH) ppm.

Sources & evidence

ORD record: ord-22d5b8e6c0304416bff960af5a72682e
Source dataset: uspto-grants-1995_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05382572

Reaction notes

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