Hexane → 5,7-Dimethoxy-1,4-dihydroquinolin-4-one

HRID 573413Notes

Reaction equation

HRID 573413 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([NH:11][CH:12]=[C:13]2[C:18](=[O:19])OC(C)(C)OC2=O)[CH:6]=[C:7]([O:9][CH3:10])[CH:8]=1.CCCCCC>C1(OC2C=CC=CC=2)C=CC=CC=1>[CH3:10][O:9][C:7]1[CH:8]=[C:3]([O:2][CH3:1])[CH:4]=[C:5]2[C:6]=1[C:18](=[O:19])[CH:13]=[CH:12][NH:11]2

Participants

4

Reactant 2

HCID 8058HexaneHCID 673176235-(((3,5-Dimethoxyphenyl)amino)methylene)-2,2-dimethyl-1,3-dioxane-4,6-dione

Product 1

HCID 435320065,7-Dimethoxy-1,4-dihydroquinolin-4-one

Reagents, catalysts & solvents 1

HCID 7583Diphenyl EtherSolvent

Procedure

5-[(3,5-Dimethoxyphenylamino)-methylene]-2,2-dimethyl[1,3]dioxane-4,6-dione (400 mg, 1.30 mmol) in diphenyl ether (5 mL) and heated at 200° C. for 30 min. The reaction mixture was cooled to rt and hexane was added and stirred for 30 min. The brown solid was filtered and dried to yield 5,7-dimethoxy-1H-quinolin-4-one LCMS m/z=206 (M+1).

Workup

  1. filtrationThe brown solid was filtered
  2. customdried

Sources & evidence

ORD record
ord-e04964cb4ea343e693c78b7834b0a156
Source dataset
uspto-grants-2015_05
Patent number
US09029538B2

Reaction notes

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