Pyridine → 2-[2-(Hydroxyamino)-2-oxoethyl]heptadecanoic acid

HRID 987855Notes

Reaction equation

HRID 987855 reaction equation
Cl.[NH2:2][OH:3].N1C=CC=CC=1.[CH2:10]([CH:26]1[CH2:31][C:30](=[O:32])[O:29][C:27]1=[O:28])[CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24]C>C(#N)C>[OH:3][NH:2][C:30](=[O:32])[CH2:31][CH:26]([CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH3:24])[C:27]([OH:29])=[O:28]

Participants

5

Reactant 3

HCID 1049PyridineHCID 778682,5-Furandione, 3-hexadecyldihydro-HCID 443297Hydroxyamine hydrochloride

Product 1

HCID 227129832-[2-(Hydroxyamino)-2-oxoethyl]heptadecanoic acid

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

HA-4 (2-[2-(hydroxyamino)-2-oxoethyl]heptadecanoic acid) was prepared as follows. Hydroxylamine hydrochloride (18.07 g, 0.26 moles) was dissolved in pyridine (18.49 g, 0.26 moles) by stirring the mixture for one-half hour at 26° C. n-Hexadecyl succinic anhydride (88.14 g, 0.27 moles, available from Tokyo Kasei Kogyo Co. Ltd., Tokyo, Japan) was added to the solution followed by the addition of acetonitrile (about 50 ml). The resulting mixture was refluxed for two hours, cooled, and the solvent removed under reduced pressure using a rotary evaporator. Hydrochloric acid (10%) in water (100 ml) was added to the resulting residue and the mixture filtered to recover the suspended solids. The filtrate was dispersed in water to dissolve the pyridinium hydrochloride by-product of the reaction and the dispersion filtered and the solid retained. The process of washing with water and filtering was repeated several times, yielding 2-[2-(hydroxyamino)-2-oxoethyl]heptadecanoic acid as a solid.

Workup

  1. customHA-4 (2-[2-(hydroxyamino)-2-oxoethyl]heptadecanoic acid) was prepared
  2. additionwas added to the solution
  3. temperatureThe resulting mixture was refluxed for two hours
  4. temperaturecooled
  5. customthe solvent removed under reduced pressure
  6. customa rotary evaporator
  7. additionHydrochloric acid (10%) in water (100 ml) was added to the resulting residue
  8. filtrationthe mixture filtered
  9. customto recover the suspended solids
  10. additionThe filtrate was dispersed in water
  11. dissolutionto dissolve
  12. customthe pyridinium hydrochloride by-product of the reaction
  13. filtrationthe dispersion filtered
  14. washThe process of washing with water
  15. filtrationfiltering

Sources & evidence

ORD record
ord-3fceb0a823c44c2d91782220f93f948e
Source dataset
uspto-grants-2003_10
Patent number
US06632872B1

Reaction notes

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