Oxalyl chloride → HCID 86753185, compound

HRID 2395415Notes

Reaction equation

HRID 2395415 reaction equation
CC1C=C([C:11]2[CH:16]=[CH:15][C:14]([O:17][CH3:18])=[C:13]([O:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=3)[CH:12]=2)C=CC=1C(O)=O.Cl.[NH2:32][OH:33].[C:34](Cl)(=[O:38])[C:35](Cl)=O>N1C=CC=CC=1>[CH3:18][O:17][C:14]1[CH:15]=[CH:16][C:11]([C:12]2[C:13]([CH3:14])=[C:35]([CH:15]=[CH:16][CH:11]=2)[C:34]([NH:32][OH:33])=[O:38])=[CH:12][C:13]=1[O:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][C:25]1[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=1

Participants

5

Reactant 3

HCID 65578Oxalyl chlorideHCID 443297Hydroxyamine hydrochlorideHCID 9822515HCID 9822515, compound

Product 1

HCID 86753185HCID 86753185, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Conditions

Temperature
25 °C

Procedure

A solution of 2-methyl-4-[4-methoxy-3-(5-phenylpentyloxy)phenyl]benzoic acid (0.13 g, 0.32 mmoles) in oxalyl chloride (5 ml) was heated to reflux under nitrogen for about 10 minutes. The solution was concentrated under reduced pressure and the residue dried at about 25° C. (0.05 mm pressure). The residue was then dissolved in dry THF (5 ml) and added slowly to a solution of hydroxylamine hydrochloride (0.022 g, 0.32 mmoles) in pyridine at about 0° C. After stirring at about 25° C. for about 16 hours the volatiles were removed under reduced pressure and the residue was slurried in 1NHCl. The mixture was then extracted with ethyl acetate and the combined organics were washed with water and brine, and dried over MgSO4. Filtration followed by concentration under reduced pressure yielded a beige solid. Recrystallization from isopropyl ether (10 ml) gave 0.055 grams of the title compound as an off-white solid. M.P. 125°-126°C.; analysis calc'd. for C26 H2 gNO4 : C,74.43; H, 6.97; N, 3.34. Found: C, 73.85; H, 6.78; N, 3.34.

Workup

  1. temperatureto reflux under nitrogen for about 10 minutes
  2. concentrationThe solution was concentrated under reduced pressure
  3. customthe residue dried at about 25° C. (0.05 mm pressure)
  4. dissolutionThe residue was then dissolved in dry THF (5 ml)
  5. customwere removed under reduced pressure
  6. extractionThe mixture was then extracted with ethyl acetate
  7. washthe combined organics were washed with water and brine
  8. dry with materialdried over MgSO4
  9. filtrationFiltration
  10. concentrationfollowed by concentration under reduced pressure
  11. customyielded a beige solid
  12. customRecrystallization from isopropyl ether (10 ml)

Sources & evidence

ORD record
ord-247fa956f2214f829c1656d5f9554c08
Source dataset
uspto-grants-1998_09
Patent number
US05814651

Reaction notes

Loading…