Acetone → 3-Fluoro-4-morpholinoaniline

HRID 1854770Notes

Reaction equation

HRID 1854770 reaction equation
CC(NC[C@@H]1OC(=O)[N:8]([C:12]2[CH:13]=[CH:14][C:15]([N:19]3[CH2:24][CH2:23][O:22][CH2:21][CH2:20]3)=[C:16]([F:18])[CH:17]=2)C1)=O.FC1C=C([N+]([O-])=O)C=CC=1N1CCOCC1.C([O-])=O.[NH4+].CC(C)=O>[Pd].C(OCC)(=O)C>[F:18][C:16]1[CH:17]=[C:12]([CH:13]=[CH:14][C:15]=1[N:19]1[CH2:24][CH2:23][O:22][CH2:21][CH2:20]1)[NH2:8]

Participants

7

Reactant 4

HCID 180AcetoneHCID 441401LinezolidHCID 2723923Ammonium formateHCID 29054894-(2-Fluoro-4-nitrophenyl)morpholine

Product 1

HCID 14853303-Fluoro-4-morpholinoanilineYield 89.5%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

It was prepared according to the literature method (ZHAO Xiao-yu, et al., Improved synthesis of Linezolid, WEST CHINA JOURNAL OF PHARMACEUTICAL SCIENCES, 2007, 22(2), 179-181). 36.2 g (0.16 mol) 3-fluoro-4-morpholinylnitrobenzene, 3.2 g 10% Pd/C, 30.4 g (0.49 mol) ammonium formate and 500 ml acetone were added into a 1000 ml four-necked bottle equipped with reflux condenser and dropping funnel, and stirred for 4 hours at 45˜50° C. After the completion of the reaction traced by TLC (developing solvent: ethyl acetate:petroleum ether=1:1), it was cooled to room temperature. After filtering by suction, solvents were evaporated from the filtrate under reduced pressure to obtain crude solid, which was recrystallized from toluene to obtain 28.1 g solid (89.5% yield). Structural confirmation:

Workup

  1. customIt was prepared
  2. customequipped
  3. temperaturewith reflux condenser
  4. filtrationAfter filtering by suction, solvents
  5. customwere evaporated from the filtrate under reduced pressure
  6. customto obtain crude solid, which
  7. customwas recrystallized from toluene

Sources & evidence

ORD record
ord-7d7f9a84fd214c389b9d60d5915331c3
Source dataset
uspto-grants-2015_02
Patent number
US08962827B2

Reaction notes

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