Diethyl Ether → HCID 10314947, compound

HRID 1382330Notes

Reaction equation

HRID 1382330 reaction equation
[CH3:1][O:2][CH2:3][C:4]([C:6]1[CH:7]=[N:8][C:9]2[C:14]([C:15]=1Cl)=[CH:13][CH:12]=[CH:11][C:10]=2[O:17][CH3:18])=[O:5].[NH2:19][C:20]1[C:21]([CH3:26])=[CH:22][CH:23]=[CH:24][CH:25]=1.CCOCC>O1CCOCC1>[CH3:18][O:17][C:10]1[CH:11]=[CH:12][CH:13]=[C:14]2[C:9]=1[N:8]=[CH:7][C:6]([C:4]([CH2:3][O:2][CH3:1])=[O:5])=[C:15]2[NH:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=1[CH3:26]

Participants

5

Reactant 3

HCID 3283Diethyl EtherHCID 7242O-ToluidineHCID 10084233HCID 10084233, compound

Product 1

HCID 10314947HCID 10314947, compoundYield 82.8%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

3-methoxyacetyl-4-chloro-8-methoxyquinoline (19.0 g, 0.07 mol) and o-toluidine (9.0 ml, 0.08 mol) were heated under reflux in 1,4-dioxan (250 ml) for 1 hour. The solvent was removed and the residue taken up in dichloromethane, washed with dilute hydrochloric acid, sodium hydrogen carbonate solution, and brine. Evaporation of the solvent gave an oil, which afforded 8-methoxy-3-methoxymethylcarbonyl-4-(2-methylphenylamino)quinoline (19.5 g, 81%) as yellow crystals from ether, m.p. 122°-3°.

Workup

  1. customThe solvent was removed
  2. washwashed with dilute hydrochloric acid, sodium hydrogen carbonate solution, and brine
  3. customEvaporation of the solvent
  4. customgave an oil, which

Sources & evidence

ORD record
ord-82a21b7944bd468eb6b831286b6d0502
Source dataset
uspto-grants-1989_02
Patent number
US04806550

Reaction notes

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