2-Methoxyaniline → HCID 10246288, compound

HRID 1382289Notes

Reaction equation

HRID 1382289 reaction equation
[C:1]([C:6]1[CH:7]=[N:8][C:9]2[C:14]([C:15]=1Cl)=[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]=[CH:25][CH:24]=[CH:23][C:21]=1[NH2:22]>O1CCCC1>[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][CH:25]=[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 70002-MethoxyanilineHCID 100376273-Butyryl-4-chloro-8-methylquinoline

Product 1

HCID 10246288HCID 10246288, compoundYield 33.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

3-Butyryl-4-chloro-8-methylquinoline (4.95 g, 20mmol), 2-methoxyaniline (4.51 ml, 40mmol) and tetrahydrofuran (20 ml) were stirred at room temperature overnight. The hydrochloride salt was filtered off, converted to free base and recrystallised from ethyl acetate/petroleum ether to give 3-butyryl-4-(2-methoxyphenylamino)-8-methylquinoline (2.25 g), m.p. 135°-137°.

Workup

  1. filtrationThe hydrochloride salt was filtered off
  2. customrecrystallised from ethyl acetate/petroleum ether

Sources & evidence

ORD record
ord-886a52f8a80c43e383d1b053e72431c9
Source dataset
uspto-grants-1989_02
Patent number
US04806549

Reaction notes

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