Potassium Hydroxide → 4-(1, 3-Benzodioxol-5-yl)-6-ethoxy-2-(2-methoxybenzyloxy)quinoline-3-carboxylic acid

HRID 2908Notes

Reaction equation

HRID 2908 reaction equation
[O:1]1[C:5]2[CH:6]=[CH:7][C:8]([C:10]3[C:19]4[C:14](=[CH:15][CH:16]=[C:17]([O:20][CH2:21][CH3:22])[CH:18]=4)[N:13](CC4C=CC=CC=4OC)[C:12](=[O:32])[C:11]=3[C:33]([O:35]C)=[O:34])=[CH:9][C:4]=2[O:3][CH2:2]1.[OH-].[K+].O1C2C=CC(C3C4C(=CC=C(OCC)C=4)N([CH2:61][C:62]4[CH:67]=[CH:66][CH:65]=[CH:64][C:63]=4[O:68][CH3:69])C(=O)C=3C(O)=O)=CC=2OC1>CO>[O:1]1[C:5]2[CH:6]=[CH:7][C:8]([C:10]3[C:19]4[C:14](=[CH:15][CH:16]=[C:17]([O:20][CH2:21][CH3:22])[CH:18]=4)[N:13]=[C:12]([O:32][CH2:61][C:62]4[CH:67]=[CH:66][CH:65]=[CH:64][C:63]=4[O:68][CH3:69])[C:11]=3[C:33]([OH:35])=[O:34])=[CH:9][C:4]=2[O:3][CH2:2]1

Participants

5

Reactant 3

HCID 14797Potassium HydroxideHCID 9913328Methyl 4-(1,3-benzodioxol-5-yl)-1,2-dihydro-6-ethoxy-1-(2-methoxybenzyl)-2-oxoquinoline-3-carboxylateHCID 102887134-(1,3-Benzodioxol-5-yl)-1,2-dihydro-6-ethoxy-1-(2-methoxybenzyl)-2-oxoquinoline-3-carboxylic acid

Product 1

HCID 224458664-(1, 3-Benzodioxol-5-yl)-6-ethoxy-2-(2-methoxybenzyloxy)quinoline-3-carboxylic acid

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 0.5 g of methyl 4-(1,3-benzodioxol-5-yl)-1,2-dihydro-6-ethoxy-1-(2-methoxybenzyl)-2-oxoquinoline-3-carboxylate and 6 ml of 5N KOH in 10 ml of methanol is boiled under reflux for 2 hours. The usual working up results in 4-(1,3-benzodioxol-5-yl)-1,2-dihydro-6-ethoxy-1-(2-methoxybenzyl)-2-oxoquinoline-3-carboxylic acid, m.p. 225°-226°. Analogously, the O-alkylation product 4-(1, 3-benzodioxol-5-yl)-6-ethoxy-2-(2-methoxybenzyloxy)quinoline-3-carboxylic acid is obtained from methyl 4-(1,3-benzodioxol-5-yl)-6-ethoxy-2-(2-methoxybenzyloxy) quinoline-3-carboxylate.

Workup

  1. temperatureunder reflux for 2 hours

Sources & evidence

ORD record
ord-3aafaa9bc09e4d7e91b49eec25c1596b
Source dataset
uspto-grants-1998_03
Patent number
US05731321

Reaction notes

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