4-Fluoro-2-methylaniline → HCID 10089362, compound

HRID 1647464Notes

Reaction equation

HRID 1647464 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]=2[CH2:17][O:18]C(=O)C1C=CC=CC=1)(=[O:5])[CH2:2][CH2:3][CH3:4].[F:27][C:28]1[CH:34]=[CH:33][C:31]([NH2:32])=[C:30]([CH3:35])[CH:29]=1>O1CCOCC1>[C:1]([C:6]1[CH:7]=[N:8][C:9]2[C:14]([C:15]=1[NH:32][C:31]1[CH:33]=[CH:34][C:28]([F:27])=[CH:29][C:30]=1[CH3:35])=[CH:13][CH:12]=[CH:11][C:10]=2[CH2:17][OH:18])(=[O:5])[CH2:2][CH2:3][CH3:4]

Participants

4

Reactant 2

HCID 679824-Fluoro-2-methylanilineHCID 19923000HCID 19923000, compound

Product 1

HCID 10089362HCID 10089362, compoundYield 44.3%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A solution of 3-butyryl-4-chloro-8-(benzoyloxymethyl)quinoline (3.68 g, 10 mmol) and 4-fluoro-2-methylaniline (1.67 ml, 15 mmol) in dioxan (40 ml) was heated at reflux for 3 hours, cooled, filtered and the solid discarded. The solution was evaporated and the residue taken up in 1% methanolic sodium hydroxide (100 ml) and stirred 2 hours at room temperature. The solid was filtered off and recrystallised from methanol to give 3-butyryl-4-(2-methyl-4-fluorophenylamino)-8-(hydroxymethyl)quinoline (1.56 g, 44%), m.p. 168°-170°.

Workup

  1. temperatureat reflux for 3 hours
  2. temperaturecooled
  3. filtrationfiltered
  4. customThe solution was evaporated
  5. filtrationThe solid was filtered off
  6. customrecrystallised from methanol

Sources & evidence

ORD record
ord-3ae5558b6bbb4cdc85deb3f6023ca3db
Source dataset
uspto-grants-1995_07
Patent number
US05432182

Reaction notes

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