O-Toluidine → HCID 19923012, compound

HRID 1647456Notes

Reaction equation

HRID 1647456 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 recrystallised from ethanol to give the title compound (1.8 g), m.p. 110°-12°.

Workup

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

Sources & evidence

ORD record
ord-1e4f084849f4451089d323ca57e910e9
Source dataset
uspto-grants-1995_07
Patent number
US05432182

Reaction notes

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