2-Methoxyaniline → HCID 21274560, compound

HRID 1382357Notes

Reaction equation

HRID 1382357 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]=2C)(=[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]>O1CCOCC1>[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][CH:10]=2)(=[O:5])[CH2:2][CH2:3][CH3:4]

Participants

4

Reactant 2

HCID 70002-MethoxyanilineHCID 100376273-Butyryl-4-chloro-8-methylquinoline

Product 1

HCID 21274560HCID 21274560, compoundYield 86.8%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

3-Butyryl-4-chloro-8-methylquinoline (2.33 g, 10 mmol), 2-methoxyaniline (1.69 ml, 15 mmol) and dioxan (10 ml) were heated at reflux for 30 minutes, then allowed to cool. The hydrochloride salt was filtered off, converted to free base and recrystallised from ethanol to give 3-butyryl-4-(2-methoxy-phenylamino)quinoline (2.78 g), m.p. 167°-168°.

Workup

  1. temperatureat reflux for 30 minutes
  2. temperatureto cool
  3. filtrationThe hydrochloride salt was filtered off
  4. customrecrystallised from ethanol

Sources & evidence

ORD record
ord-771acb4fded84f84ad1e426c16f5991d
Source dataset
uspto-grants-1989_02
Patent number
US04806550

Reaction notes

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