Pyridinium chloride → HCID 21071779, compound

HRID 1372140Notes

Reaction equation

HRID 1372140 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([C:10]2[C:19]3[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=3)[C:13]([CH:20]=[O:21])=[CH:12][CH:11]=2)[CH:5]=[CH:6][C:7]=1[O:8]C.Cl.N1C=CC=CC=1>O>[F:1][C:2]1[CH:3]=[C:4]([C:10]2[C:19]3[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=3)[C:13]([CH:20]=[O:21])=[CH:12][CH:11]=2)[CH:5]=[CH:6][C:7]=1[OH:8]

Participants

4

Reactant 2

HCID 10176127Pyridinium chloride2×HCID 21071780HCID 21071780, compound

Product 1

HCID 21071779HCID 21071779, compoundYield 104.4%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
195 °C

Procedure

To a 35 ml flask was added 4-(3-fluoro-4-methoxyphenyl)-naphthalene-1-carbaldehyde (720 mg ˜80% pure, 2.05 mmol), and pyridine hydrochloride (3 g, 26 mmol). The mixture was warmed to 195° C. for 2 h, cooled slightly, and the remaining pyridine hydrochloride was dissolved in water (50 ml). The aqueous layer was extracted with ethyl acetate (3×), dried over anhydrous Na2SO4, passed through a silica plug and concentrated to afford 570 mg (99%) of product as an off-white foam. The material was carried on to the next step without further purification: 1H NMR (300 MHz, DMSO-d6) δ 7.16 (2H, m), 7.35 (1H, d, J=12.00 Hz), 7.60–7.80 (3H, m), 7.98 (2H, d, J=8.3 Hz) 8.22 (1H, d, J=7.4 Hz), 9.28 (1H, d, J=8.4), 10.24 (1H, s), 10.43 (1H, s).

Workup

  1. temperaturecooled slightly
  2. extractionThe aqueous layer was extracted with ethyl acetate (3×)
  3. dry with materialdried over anhydrous Na2SO4
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-a05be91fa2644c8b8777dc006ab144f3
Source dataset
uspto-grants-2007_01
Patent number
US07157491B2

Reaction notes

Loading…