3-Aminobiphenyl → HCID 67406221, compound

HRID 1056876Notes

Reaction equation

HRID 1056876 reaction equation
[CH2:1]([O:8][C:9]1[C:10](=[O:17])[CH:11]=[C:12]([CH2:15][OH:16])O[CH:14]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:18]1([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[CH:23]=[CH:22][CH:21]=[C:20]([NH2:24])[CH:19]=1>Cl>[CH2:1]([O:8][C:9]1[C:10](=[O:17])[CH:11]=[C:12]([CH2:15][OH:16])[N:24]([C:20]2[CH:19]=[C:18]([C:25]3[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=3)[CH:23]=[CH:22][CH:21]=2)[CH:14]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 167173-AminobiphenylHCID 9015985-(benzyloxy)-2-(hydroxymethyl)-4H-pyran-4-one

Product 1

HCID 67406221HCID 67406221, compound

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

To a suspension of 5-(benzyloxy)-2-(hydroxymethyl)-4H-pyran-4-one (92.9 g, 0.40 mol) in dilute aq hydrochloric acid (0.5 N, 800 mL) was added biphenyl-3-amine (74.4 g, 0.44 mol). The resulting mixture was heated under refluxed for 16 h. Concentration of the solvent gave a residue which was purified by silica gel chromatography (EtOAc:MeOH/20:1) to afford 5-(benzyloxy)-1-(biphenyl-3-yl)-2-(hydroxymethyl)pyridin-4(1H)-one as pale solid MS (ESI) (M+H)+ 384.

Workup

  1. temperatureThe resulting mixture was heated
  2. temperatureunder refluxed for 16 h
  3. customConcentration of the solvent gave a residue which
  4. customwas purified by silica gel chromatography (EtOAc:MeOH/20:1)

Sources & evidence

ORD record
ord-4adb1706f8bd47139b880732521f555f
Source dataset
uspto-grants-2016_07
Patent number
US09399651B2

Reaction notes

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