Ethyl acetate hexane → HCID 178467004, compound

HRID 2405820Notes

Reaction equation

HRID 2405820 reaction equation
C(O[C:4](=[O:20])[CH2:5][C:6]([O:17][CH2:18][CH3:19])=[N:7][C:8]1[CH:13]=[CH:12][CH:11]=[C:10]([O:14][CH3:15])[C:9]=1[CH3:16])C.CCOC(C)=O.CCCCCC>C1(OC2C=CC=CC=2)C=CC=CC=1>[CH2:18]([O:17][C:6]1[CH:5]=[C:4]([OH:20])[C:13]2[C:8](=[C:9]([CH3:16])[C:10]([O:14][CH3:15])=[CH:11][CH:12]=2)[N:7]=1)[CH3:19]

Participants

4

Reactant 2

HCID 21226206Ethyl acetate hexaneHCID 576034223-Ethoxy-3-(3-methoxy-2-methyl-phenylimino)-propionic acid ethyl ester

Product 1

HCID 178467004HCID 178467004, compoundYield 68%

Reagents, catalysts & solvents 1

HCID 7583Diphenyl EtherSolvent

Procedure

3-Ethoxy-3-(3-methoxy-2-methyl-phenylimino)-propionic acid ethyl ester (1.56 g, 5.57 mmol) was dissolved in diphenyl ether then placed in a 300° C. sand bath. The internal temperature was kept between 240-250° C. for 15 minutes then the reaction was cooled to room temperature. The crude material was directly loaded onto a silica gel column (0→60% EtOAc/hexane) to afford 2-ethoxy-7-methoxy-8-methyl-quinolin-4-ol (882 mg, 68%). LCMS found 234.1 [M+H]+.

Workup

  1. customthen placed in a 300° C.

Sources & evidence

ORD record
ord-fb23a9f8ac9c47c188c7594408767c34
Source dataset
uspto-grants-2014_08
Patent number
US08809267B2

Reaction notes

Loading…