Water → HCID 14555675, compound

HRID 1723411Notes

Reaction equation

HRID 1723411 reaction equation
Cl.[NH2:2][OH:3].C(=O)([O-])[O-].[Na+].[Na+].[CH3:10][O:11][C:12]1[CH:13]=[C:14]([CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][C:26](Cl)=[O:27])[CH:15]=[CH:16][CH:17]=1.O>C(Cl)Cl>[CH3:10][O:11][C:12]1[CH:13]=[C:14]([CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][C:26]([NH:2][OH:3])=[O:27])[CH:15]=[CH:16][CH:17]=1

Participants

6

Reactant 4

HCID 962Water2×HCID 10340Sodium CarbonateHCID 443297Hydroxyamine hydrochlorideHCID 20025670HCID 20025670, compound

Product 1

HCID 14555675HCID 14555675, compoundYield 33.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a cold stirred suspension of 0.7 gms hydroxylamine hydrochloride and 1 gm sodium carbonate in 10 ml CH2Cl2 was added a solution of 2.1 gms 9(3-methoxyphenyl)nonanoyl chloride in 10 ml CH2Cl2. After stirring this mixture for 1/2 hr, 1.1 ml H2O was added, and the reaction was stirred overnight at room temperature. 30 ml water was added, the layers were separated, and the aqueous layer 3×50 ml extracted with CH2Cl2. The organic phases were combined, washed 2×20 ml water, 2×20 ml NaCl solution, dried over MgSO4, filtered, and evaporated in vacuo to give an oil which solidified on standing. The solid was crystallized from CH2Cl2 :hexanes but was still impure by thin layer chromatography. It was dissolved in 100 ml CHCl3, stirred with 20 gm silica gel, and filtered. The silica gel was suspended in 75 ml CHCl3, stirred, and filtered (process repeated three times). All filtrates were combined, evaporated in vacuo, and the residue recrystallized from CH2Cl2 :hexanes to give 0.7 gms product of m.p. 66°-8°. Elemental analysis: calculated C 68.79, H 9.02, N 5.01% found C 68.61, H 9.18, N 5.09%.

Workup

  1. stirringAfter stirring this mixture for 1/2 hr
  2. stirringthe reaction was stirred overnight at room temperature
  3. customthe layers were separated
  4. extractionthe aqueous layer 3×50 ml extracted with CH2Cl2
  5. washwashed 2×20 ml water, 2×20 ml NaCl solution
  6. dry with materialdried over MgSO4
  7. filtrationfiltered
  8. customevaporated in vacuo
  9. customto give an oil which
  10. customThe solid was crystallized from CH2Cl2
  11. dissolutionIt was dissolved in 100 ml CHCl3
  12. stirringstirred with 20 gm silica gel
  13. filtrationfiltered
  14. stirringstirred
  15. filtrationfiltered (process repeated three times)
  16. customevaporated in vacuo
  17. customthe residue recrystallized from CH2Cl2

Sources & evidence

ORD record
ord-4bbfe68930f143719b2a322b9335d9c3
Source dataset
uspto-grants-1989_08
Patent number
US04861798

Reaction notes

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