2-Methoxyaniline → HCID 21274560, compound

HRID 1382305Notes

Reaction equation

HRID 1382305 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-8c6c284fe07c495c903ecc3bb9a777de
Source dataset
uspto-grants-1989_02
Patent number
US04806549

Reaction notes

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