2,4-Dimethoxyaniline → HCID 21274554, compound

HRID 1382291Notes

Reaction equation

HRID 1382291 reaction equation
[C:1]([C:6]1[CH:7]=[N:8][C:9]2[C:14]([C:15]=1[Cl:16])=[CH:13][CH:12]=[CH:11][C:10]=2[CH3:17])(=[O:5])[CH2:2][CH2:3][CH3:4].[CH3:18][O:19][C:20]1[CH:26]=[C:25]([O:27][CH3:28])[CH:24]=[CH:23][C:21]=1[NH2:22]>O1CCOCC1>[ClH:16].[C:1]([C:6]1[CH:7]=[N:8][C:9]2[C:14]([C:15]=1[NH:22][C:21]1[CH:23]=[CH:24][C:25]([O:27][CH3:28])=[CH:26][C:20]=1[O:19][CH3:18])=[CH:13][CH:12]=[CH:11][C:10]=2[CH3:17])(=[O:5])[CH2:2][CH2:3][CH3:4]

Participants

4

Reactant 2

HCID 176522,4-DimethoxyanilineHCID 100376273-Butyryl-4-chloro-8-methylquinoline

Product 1

HCID 21274554HCID 21274554, compoundYield 57%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

3-Butyryl-4-chloro-8-methylquinoline (2.48 g, 10 mmol), 2,4-dimethoxyaniline (3.06 g, 20 mmol) and 1,4-dioxan (20 ml) were heated at reflux for 1.5 hours. the solvent evaporated, the residue taken up in dichloromethane, washed with aqueous sodium bicarbonate, dried and evaporated. Chromatography (silica gel, 1% methanol in chloroform), conversion to the hydrochloride salt and recrystallisation from aqueous methanol gave 3-butyryl-4-(2,4-dimethoxyphenylamino)-8-methylquinoline hydrochloride (2.10 g, 57%), m.p. 190°-192°.

Workup

  1. temperatureat reflux for 1.5 hours
  2. customthe solvent evaporated
  3. washwashed with aqueous sodium bicarbonate
  4. customdried
  5. customevaporated
  6. customChromatography (silica gel, 1% methanol in chloroform), conversion to the hydrochloride salt and recrystallisation from aqueous methanol

Sources & evidence

ORD record
ord-7b4d4fc1e7f7414683ba537010cf705a
Source dataset
uspto-grants-1989_02
Patent number
US04806549

Reaction notes

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