4-Fluoro-1-benzofuran-3(2H)-one → 2,3-Dihydro-1-benzofuran-3-amine

HRID 1363202Notes

Reaction equation

HRID 1363202 reaction equation
F[C:2]1[C:7]2[C:8](=[N:11]O)[CH2:9][O:10][C:6]=2[CH:5]=[CH:4][CH:3]=1.FC1C2C(=O)COC=2C=CC=1>CO.[Pd]>[O:10]1[C:6]2[CH:5]=[CH:4][CH:3]=[CH:2][C:7]=2[CH:8]([NH2:11])[CH2:9]1

Participants

5

Reactant 2

HCID 451226514-Fluoro-1-benzofuran-3(2H)-oneHCID 72368497HCID 72368497, compound

Product 1

HCID 137781522,3-Dihydro-1-benzofuran-3-amine

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To the solution of benzofuran-3(2H)-one oxime (1.0 g, obtained from commercially available benzofuran-3(2H)-one via the procedure outlined for the synthesis of 4-fluorobenzofuran-3(2H)-one oxime from 4-fluorobenzofuran-3(2H)-one) in 50 mL MeOH, 10% Palladium on active carbon (0.1 g) was added. The mixture was evacuated then filled with H2 three times. Finally the oxime was reduced under a H2 balloon for 24 hours. The mixture was filtered through a pad of celite, and the cake was washed with MeOH twice. After removing the solvents under vacuum, 0.99 g brown-yellow residue was obtained as the desired amine. 1H NMR (300 MHz, CDCl3): δ 7.32 (d, 1H), 7.19 (t, 1H), 6.94 (t, 1H), 6.82 (d, 1H), 4.5-4.7 (m, 1H), 4.64 (s, 1H), 4.1-4.2 (m, 1H).

Workup

  1. customThe mixture was evacuated
  2. additionthen filled with H2 three times
  3. customfor 24 hours
  4. filtrationThe mixture was filtered through a pad of celite
  5. washthe cake was washed with MeOH twice
  6. customAfter removing the solvents under vacuum

Sources & evidence

ORD record
ord-09965227c4994da198f828f7ff7e1e79
Source dataset
uspto-grants-2011_02
Patent number
US07884109B2

Reaction notes

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