2-Methyl-4-methoxyaniline → HCID 10405472, compound

HRID 1382290Notes

Reaction equation

HRID 1382290 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][C:23]([NH2:24])=[C:22]([CH3:27])[CH:21]=1>O1CCOCC1>[C:1]([C:6]1[CH:7]=[N:8][C:9]2[C:14]([C:15]=1[NH:24][C:23]1[CH:25]=[CH:26][C:20]([O:19][CH3:18])=[CH:21][C:22]=1[CH3:27])=[CH:13][CH:12]=[CH:11][C:10]=2[CH3:17])(=[O:5])[CH2:2][CH2:3][CH3:4]

Participants

4

Reactant 2

HCID 76102-Methyl-4-methoxyanilineHCID 100376273-Butyryl-4-chloro-8-methylquinoline

Product 1

HCID 10405472HCID 10405472, compoundYield 76.1%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

3-Butyryl-4-chloro-8-methylquinoline (4.95 g, 20 mmol), 4-methoxy-2-methylaniline (5.15 ml, 40 mmol) and 1,4-dioxan (20 ml) were heated at reflux for 1 hour, the solvent evaporated, the residue taken up in dichloromethane, washed with aqueous sodium bicarbonate, dried and evaporated. Recrystallisation from methanol gave 3-butyryl-4-(4-methoxy-2-methylphenylamino)-8-methylquinoline (5.30 g), m.p. 114°-115°.

Workup

  1. temperatureat reflux for 1 hour
  2. customthe solvent evaporated
  3. washwashed with aqueous sodium bicarbonate
  4. customdried
  5. customevaporated
  6. customRecrystallisation from methanol

Sources & evidence

ORD record
ord-e992b50befaf41e1bb7de2c6722a0657
Source dataset
uspto-grants-1989_02
Patent number
US04806549

Reaction notes

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