Ammonium formate → 4-Fluoro-2-(oxan-4-yloxy)aniline

HRID 450532Notes

Reaction equation

HRID 450532 reaction equation
C([O-])=O.[NH4+].[F:5][C:6]1[CH:7]=[CH:8][C:9]([N+:19]([O-])=O)=[C:10]([CH:18]=1)[O:11][CH:12]1[CH2:17][CH2:16][O:15][CH2:14][CH2:13]1>[Pd].CO>[F:5][C:6]1[CH:7]=[CH:8][C:9]([NH2:19])=[C:10]([O:11][CH:12]2[CH2:17][CH2:16][O:15][CH2:14][CH2:13]2)[CH:18]=1

Participants

5

Reactant 2

HCID 2723923Ammonium formateHCID 533521804-(5-fluoro-2-nitrophenoxy)tetrahydro-2H-pyran

Product 1

HCID 584130794-Fluoro-2-(oxan-4-yloxy)anilineYield 76.2%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

Ammonium formate (1.11 g, 17.6 mmol) was added into a suspension of 4-(5-fluoro-2-nitrophenoxy)tetrahydro-2H-pyran (1 g, 4.14 mmol) and palladium on carbon (5%, 0.250 g) in MeOH (10 mL) at ambient temperature. The solution was stirred for 0.5 hours, filtered through Celite and washed with MeOH. The filtrate was concentrated in vacuo and triturated from diethyl ether to remove the ammonium formate by-products. The sample was purified by flash column chromatography (5:1 petroleum ether (40-60° C.)/EtOAc→1:1 petroleum ether (40-60° C.)/EtOAc) to yield yellow oil (0.666 g, 76%).

Workup

  1. filtrationfiltered through Celite
  2. washwashed with MeOH
  3. concentrationThe filtrate was concentrated in vacuo
  4. customtriturated from diethyl ether
  5. customto remove the ammonium formate by-products
  6. customThe sample was purified by flash column chromatography (5:1 petroleum ether (40-60° C.)/EtOAc→1:1 petroleum ether (40-60° C.)/EtOAc)

Sources & evidence

ORD record
ord-0b75d13b4f324b14b5a3e3f5e5e35679
Source dataset
uspto-grants-2013_07
Patent number
US08486953B2

Reaction notes

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