O-Toluidine → 2-Methylphenylamino-8-(4-methoxybenzoyloxymethyl)quinoline

HRID 1534463Notes

Reaction equation

HRID 1534463 reaction equation
C([C:6]1[CH:7]=[N:8][C:9]2[C:14]([C:15]=1Cl)=[CH:13][CH:12]=[CH:11][C:10]=2[CH2:17][O:18][C:19](=[O:28])[C:20]1[CH:25]=[CH:24][C:23]([O:26][CH3:27])=[CH:22][CH:21]=1)(=O)CCC.C[C:30]1[CH:36]=[CH:35][CH:34]=[CH:33][C:31]=1[NH2:32].O1CCOC[CH2:38]1>>[CH3:38][C:7]1[C:6]([NH:32][C:31]2[CH:33]=[CH:34][CH:35]=[CH:36][CH:30]=2)=[CH:15][C:14]2[C:9](=[C:10]([CH2:17][O:18][C:19](=[O:28])[C:20]3[CH:25]=[CH:24][C:23]([O:26][CH3:27])=[CH:22][CH:21]=3)[CH:11]=[CH:12][CH:13]=2)[N:8]=1

Participants

4

Reactant 3

HCID 7242O-ToluidineHCID 312751,4-DioxaneHCID 104534453-Butyryl-4-chloro-8-(4-methoxybenzoyloxymethyl)quinoline

Product 1

HCID 867454832-Methylphenylamino-8-(4-methoxybenzoyloxymethyl)quinolineYield 90%

Procedure

A solution of 3-butyryl-4-chloro-8-(4-methoxybenzoyloxymethyl)-quinoline 3.3 g, 8.3 mmol) and 2-methylaniline (1.33 ml, 12.4 mmol) in 1,4-dioxan (30 ml) was heated at reflux for 2 hours, then the dioxan evaporated and the product converted to free base. Recyrstallization from ethanol gave 3-butyryl-4-(2-methylphenylamino-8-(4-methoxybenzoyloxymethyl)-quinoline (3.5 g, 90%), m.p. 135°-137°.

Workup

  1. temperatureat reflux for 2 hours
  2. customthe dioxan evaporated

Sources & evidence

ORD record
ord-8b253a3bcab246bdb6db4c57a90957ab
Source dataset
uspto-grants-1992_02
Patent number
US05089504

Reaction notes

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