Isatoic Anhydride → 1-Heptyl-3-Ethoxycarbonyl-4-Methoxy-2(1H)-Quinolinone

HRID 36055

Reaction equation

HRID 36055 reaction equation
[C:1]12C(=CC=CC=1)NC(=O)OC2=O.[CH2:13]([N:20]1[C:29]2[C:24](=[CH:25][CH:26]=[CH:27][CH:28]=2)[C:23]([OH:30])=[C:22]([C:31]([O:33][CH2:34][CH3:35])=[O:32])[C:21]1=[O:36])[CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH3:19].[N+](=C)=[N-]>CCOCC>[CH2:13]([N:20]1[C:29]2[C:24](=[CH:25][CH:26]=[CH:27][CH:28]=2)[C:23]([O:30][CH3:1])=[C:22]([C:31]([O:33][CH2:34][CH3:35])=[O:32])[C:21]1=[O:36])[CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH3:19]

Participants

5

Reactant 3

HCID 8359Isatoic AnhydrideHCID 9550DiazomethaneHCID 546847811-Heptyl-3-Ethoxycarbonyl-4-Hydroxy-2(1H)-Quinolinone

Product 1

HCID 212178031-Heptyl-3-Ethoxycarbonyl-4-Methoxy-2(1H)-Quinolinone

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

Following the procedure set forth in Preparation A, steps (2-3), isatoic anhydride was converted to 1-heptyl-4-hydroxy-3-ethoxycarbonyl-2(1H)-quinolinone, which upon reaction with excess diazomethane in ether gave the title compound. That the expected product was obtained was confirmed by the spectral data: MS: m/e 345 (M+).

Sources & evidence

ORD record
ord-f2f1ff701b9b4467a519f5737562da63
Source dataset
uspto-grants-1995_05
Patent number
US05412104

Linked notes

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