Hydrochloric Acid → 2-(4'-Methoxyphenyl)-5-octyloxypyridine

HRID 1768883Notes

Reaction equation

HRID 1768883 reaction equation
Cl.[CH2:2]([O:10][C:11]1[CH:19]=[CH:18][C:14]([C:15]([NH2:17])=N)=[CH:13][CH:12]=1)CCCCCCC.[CH2:20]([O:28][C:29]1[CH:34]=CC(C#N)=[CH:31][CH:30]=1)[CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH3:27].C(=O)([O-])[O-].[Na+].[Na+].Cl>C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[Pd].C1(C)C=CC=CC=1>[CH3:2][O:10][C:11]1[CH:12]=[CH:13][C:14]([C:15]2[CH:31]=[CH:30][C:29]([O:28][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH3:27])=[CH:34][N:17]=2)=[CH:18][CH:19]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 10340Sodium CarbonateHCID 1451614-(Octyloxy)benzonitrileHCID 122385044-n-Octyloxybenzamidine hydrochloride

Product 1

HCID 200979682-(4'-Methoxyphenyl)-5-octyloxypyridine

Reagents, catalysts & solvents 2

HCID 11979704Tetrakis(triphenylphosphine)palladiumCatalystHCID 1140TolueneSolvent

Procedure

To a flask outfitted with a reflux condenser was added 6B (300 mg), 6A (600 mg), and palladium tetrakis(triphenylphosphine) (62 mg). To this mixture was added toluene (4 ml) and a sodium carbonate solution (2M, 4.5 ml). This solution was refluxed for 16 hrs, at which time it was acidified with hydrochloric acid and extracted with ethyl acetate. The combined organic layers were washed with brine and dried over sodium sulfate and potassium carbonate. The solvent was removed in vacuo. The product purified by flash chromatography using 20% ethyl acetate in hexanes as the eluent to give a yellow liquid.

Workup

  1. customTo a flask outfitted with a reflux condenser
  2. temperatureThis solution was refluxed for 16 hrs, at which time it
  3. extractionextracted with ethyl acetate
  4. washThe combined organic layers were washed with brine
  5. dry with materialdried over sodium sulfate and potassium carbonate
  6. customThe solvent was removed in vacuo
  7. customThe product purified by flash chromatography
  8. customto give a yellow liquid

Sources & evidence

ORD record
ord-c2f4df1617b9419dbda3909c028e5f37
Source dataset
uspto-grants-1995_01
Patent number
US05380460

Reaction notes

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