O-Toluidine → HCID 10380322, compound

HRID 1382356Notes

Reaction equation

HRID 1382356 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][CH:10]=2)(=[O:5])[CH2:2][CH2:3][CH3:4].[CH3:17][C:18]1[CH:24]=[CH:23][CH:22]=[CH:21][C:19]=1[NH2:20]>O1CCOCC1>[C:1]([C:6]1[CH:7]=[N:8][C:9]2[C:14]([C:15]=1[NH:20][C:19]1[CH:21]=[CH:22][CH:23]=[CH:24][C:18]=1[CH3:17])=[CH:13][CH:12]=[CH:11][CH:10]=2)(=[O:5])[CH2:2][CH2:3][CH3:4]

Participants

4

Reactant 2

HCID 7242O-ToluidineHCID 10466538HCID 10466538, compound

Product 1

HCID 10380322HCID 10380322, compoundYield 59.1%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

3-Butyryl-4-chloroquinoline (2.33 g, 10 mmol), 2-methylaniline (1.60 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 aqueous ethanol to give 3-butyryl-4-(2-methylphenylamino)quinoline (1.80 g), m.p. 107°-109°. PG,35

Workup

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

Sources & evidence

ORD record
ord-c410f3d809434b70b02a9aea7b776528
Source dataset
uspto-grants-1989_02
Patent number
US04806550

Reaction notes

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