O-Toluidine → HCID 19923012, compound

HRID 1534474Notes

Reaction equation

HRID 1534474 reaction equation
[C:1]([C:6]1[CH:7]=[N:8][C:9]2[C:14]([C:15]=1Cl)=[CH:13][CH:12]=[C:11]([CH2:17][O:18][C:19](=[O:26])[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)[CH:10]=2)(=[O:5])[CH2:2][CH2:3][CH3:4].[NH2:27][C:28]1[C:29]([CH3:34])=[CH:30][CH:31]=[CH:32][CH:33]=1>O1CCOCC1>[C:1]([C:6]1[CH:7]=[N:8][C:9]2[C:14]([C:15]=1[NH:27][C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][C:29]=1[CH3:34])=[CH:13][CH:12]=[C:11]([CH2:17][O:18][C:19](=[O:26])[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)[CH:10]=2)(=[O:5])[CH2:2][CH2:3][CH3:4]

Participants

4

Reactant 2

HCID 7242O-ToluidineHCID 10338985HCID 10338985, compound

Product 1

HCID 19923012HCID 19923012, compoundYield 41%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

3-butyryl-4-chloro-7-benzoyloxymethylquinoline (3.68 g, 10 mmol) and o-toluidine (1.61 g, 15 mmol) in dioxan (100 ml) were refluxed for 2.5 hours, then allowed to cool and stand for 16 hours. The solvent was evaporated and the product converted to the free base and recrystallized from ethanol to give the title compound (1.8 g) m.p. 110°-12°.

Workup

  1. temperatureto cool
  2. customThe solvent was evaporated
  3. customrecrystallized from ethanol

Sources & evidence

ORD record
ord-1f48f0afd42e46c8a98308104274e7e7
Source dataset
uspto-grants-1992_02
Patent number
US05089504

Reaction notes

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