HCID 58485966, compound → 3-[1-(3-aminophenyl)ethyl]-5,6-difluoro-3H-benzoxazol-2-one

HRID 655316Notes

Reaction equation

HRID 655316 reaction equation
[F:1][C:2]1[C:3]([F:23])=[CH:4][C:5]2[O:9][C:8](=[O:10])[N:7]([CH:11]([C:13]3[CH:18]=[CH:17][CH:16]=[C:15]([N+:19]([O-])=O)[CH:14]=3)[CH3:12])[C:6]=2[CH:22]=1>C1COCC1.[Ni]>[NH2:19][C:15]1[CH:14]=[C:13]([CH:11]([N:7]2[C:6]3[CH:22]=[C:2]([F:1])[C:3]([F:23])=[CH:4][C:5]=3[O:9][C:8]2=[O:10])[CH3:12])[CH:18]=[CH:17][CH:16]=1

Participants

4

Reactant 1

HCID 58485966HCID 58485966, compound

Product 1

HCID 584861083-[1-(3-aminophenyl)ethyl]-5,6-difluoro-3H-benzoxazol-2-one

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 8028TetrahydrofuranSolvent

Procedure

633 mg (1.98 mmol) of 5,6-difluoro-3-[1-(3-nitrophenyl)ethyl]-3H-benzoxazol-2-one are dissolved in 10 ml of THF and hydrogenated under a hydrogen atmosphere using 700 mg of Raney nickel (water-wet). After 24 h, the reaction solution is filtered, the filtrate is evaporated to dryness, and the residue is crystallised from diethyl ether/petroleum ether.

Workup

  1. filtrationthe reaction solution is filtered
  2. customthe filtrate is evaporated to dryness
  3. customthe residue is crystallised from diethyl ether/petroleum ether

Sources & evidence

ORD record
ord-08e21687a02943b285358f463e873892
Source dataset
uspto-grants-2011_12
Patent number
US08071593B2

Reaction notes

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