3-Fluorobenzylamine → HCID 54724205, compound

HRID 1831978Notes

Reaction equation

HRID 1831978 reaction equation
[OH:1][C:2]1[CH:7]=[C:6]([CH3:8])O[C:4](=[O:9])[CH:3]=1.[F:10][C:11]1[CH:12]=[C:13]([CH:16]=[CH:17][CH:18]=1)[CH2:14][NH2:15]>C(O)CCC>[F:10][C:11]1[CH:12]=[C:13]([CH:16]=[CH:17][CH:18]=1)[CH2:14][N:15]1[C:6]([CH3:8])=[CH:7][C:2]([OH:1])=[CH:3][C:4]1=[O:9]

Participants

4

Reactant 2

HCID 668533-FluorobenzylamineHCID 546757574-Hydroxy-6-methyl-2-pyrone

Product 1

HCID 54724205HCID 54724205, compoundYield 18.4%

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent

Procedure

A mixture of 4-hydroxy-6-methyl-2-pyrone (2.5 g, 0.02 mol) and 3-fluorobenzylamine (2.5 g, 0.02 mol) in n-butanol (15.0 mL) was heated to reflux for 16 h under argon atmosphere. Butanol wad distilled in vacuo, the residue was triturated with EtOAc, cooled and filterd the precipitate. It was washed with cold EtOAc, and dried to give 0.86 g of the title compound as a pale yellow powder: 1H-NMR (CD3OD/400 MHz) δ 7.31 (m, 1H), 7.0-6.85 (m, 2H), 6.83 (d, 1H, J=9.6 Hz), 5.96 (d, 1H, j=2.0 Hz), 5.80 (d, 1H, J=2.0 Hz), 5.30 (s, 2H), and 2,24 (s, 3H); ES MS m/z 234 (MH+). Step 2: Preparation of 3-bromo-1-(3-fluorobenzyl)-4-hydroxy-6-methylpyridin-2(1H)-one

Workup

  1. temperaturewas heated
  2. temperatureto reflux for 16 h under argon atmosphere
  3. distillationButanol wad distilled in vacuo
  4. customthe residue was triturated with EtOAc
  5. temperaturecooled
  6. washIt was washed with cold EtOAc
  7. customdried

Sources & evidence

ORD record
ord-96214eac87294e609aaef56fc34cd4f0
Source dataset
uspto-grants-2006_06
Patent number
US07067540B2

Reaction notes

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