Water → HCID 14555680, compound

To a cold, stirring suspension of 0.6 gm of N-methyl hydroxylamine hydrochloride and 0.7 gms sodium carbonate in 15 ml CH2Cl2 was added dropwise 2 gms 9(4-hexyloxyphenyl)nonanoyl chloride. The resulting mixture was stirred in the cold for 1/2 hr, then 0.9 ml water was added and the reaction stirred at room temperature for 22 hr. 100 ml CH2Cl2 and 40 ml water was added, and the pH of the aqueous layer was adjusted to 3-4 with a few drops of conc. HCl. The organic layers were separated and the aqueous layer was 3×20 ml CH2Cl2 extracted. The combined organic extracts were washed with water and NaCl solution, and dried over MgSO4. The drying agent was filtered off, the solvent was evaporated in vacuo, and the residue was purified by column chromatography on silica gel in chloroform. The major component had R=0.2. The fractions containing product (as determined by thin layer chromatography) were combined, evaporated in vacuo and the resulting solid recrystallized from hexanes to give 1.0 gm product of m.p. 59°-61°. Elemental analysis calculated C 72.69, H 10.26, N 3.85, O 13.2% found C 72.54, N 10.46, N 3.98%.

1. stirringThe resulting mixture was stirred in the cold for 1/2 hr
2. stirringthe reaction stirred at room temperature for 22 hr
3. customThe organic layers were separated
4. extractionextracted
5. washThe combined organic extracts were washed with water and NaCl solution
6. dry with materialdried over MgSO4
7. filtrationThe drying agent was filtered off
8. customthe solvent was evaporated in vacuo
9. customthe residue was purified by column chromatography on silica gel in chloroform
10. additionThe fractions containing product (as determined by thin layer chromatography)
11. customevaporated in vacuo
12. customthe resulting solid recrystallized from hexanes

ORD record

ord-8742a20dbb86423eb1af36492391e9e6

Source dataset

uspto-grants-1989_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04861798