Diethyl Ether → HCID 54691271, compound

HRID 1493573Notes

Reaction equation

HRID 1493573 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[C:5]([NH2:9])[CH:4]=1.[CH3:10][O:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=1[CH:18]([C:24](OCC)=[O:25])[C:19](OCC)=[O:20].C(OCC)C>C1(OC2C=CC=CC=2)C=CC=CC=1>[OH:25][C:24]1[C:6]2[C:5](=[CH:4][C:3]([O:2][CH3:1])=[CH:8][CH:7]=2)[NH:9][C:19](=[O:20])[C:18]=1[C:13]1[CH:14]=[CH:15][CH:16]=[CH:17][C:12]=1[O:11][CH3:10]

Participants

5

Reactant 3

HCID 3283Diethyl EtherHCID 108243-MethoxyanilineHCID 12858907HCID 12858907, compound

Product 1

HCID 54691271HCID 54691271, compoundYield 90.7%

Reagents, catalysts & solvents 1

HCID 7583Diphenyl EtherSolvent

Conditions

Temperature
280 °C

Procedure

A mixture of 2.7 g of m-anisidine and 5.32 g of diethyl 2-methoxyphenylmalonate in 20 ml of diphenyl ether was placed in a flask equipped with an air condenser, and heated at 270-290° C. for 2.5 hours. After cooling, to the reaction mixture there was added 80 ml of diethyl ether. The precipitates were collected by filtration, and washed with diethyl ether to obtain 5.39 g of 4-hydroxy-7-methoxy-3-(2-methoxyphenyl)-2-quinolone (yield: 90.7%).

Workup

  1. customwas placed in a flask
  2. customequipped with an air condenser
  3. temperatureAfter cooling, to the reaction mixture there
  4. filtrationThe precipitates were collected by filtration
  5. washwashed with diethyl ether

Sources & evidence

ORD record
ord-3791a1e5014145f08ea941c0802dc91c
Source dataset
uspto-grants-1991_06
Patent number
US05023261

Reaction notes

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