Hydrochloric Acid → HCID 14555670, compound

HRID 1723406Notes

Reaction equation

HRID 1723406 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([CH2:8][CH2:9][C:10](=O)[CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][C:16]([OH:18])=[O:17])[CH:5]=[CH:6][CH:7]=1.O.NN.[OH-].[K+].N#N.Cl>C(O)COCCO.O>[CH3:1][C:2]1[CH:3]=[C:4]([CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][C:16]([OH:18])=[O:17])[CH:5]=[CH:6][CH:7]=1

Participants

8

Reactant 5

HCID 313Hydrochloric AcidHCID 947NitrogenHCID 14797Potassium HydroxideHCID 24654Hydrazine hydrate (1:1)HCID 14555667HCID 14555667, compound

Product 1

HCID 14555670HCID 14555670, compoundYield 61%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 8117Diethylene GlycolSolvent

Conditions

Temperature
70 °C

Procedure

To a stirred solution of 66 gm 9(3-methylphenyl)-7-ketononanoic acid in 35 ml diethylene glycol was added 4.3 ml hydrazine hydrate. The reaction mixture was heated at 120° for 5 hrs, cooled to 70° C., connected to a water aspirator, and re-heated to 120°-30° for 31/2 hrs. The mixture was then cooled to 70°, 6.5 g KOH was added, and the reaction mixture was heated to 160°-200° (temperature varied with N2 evolution) for 11 hr, then cooled to room temperature. The solidified reaction mass was dissolved in 150 ml hot water, acidified with conc. HCl, three times extracted with CHCl3 and the organic phases were combined. They were washed three times with water, once with saturated NaCl solution, dried over MgSO4, filtered, treated with charcoal, filtered through diatomaceous earth, and the solvent was removed in vacuo to give a brown oil which was vacuum distilled. Yield 61%. The main fraction boiled at 170°-80° at 0.1 mm and later solidified to a product of m.p. 39°-40°. Elemental analysis: calculated C 77.37, H 9.74. Found: C 77.25, H 9.98.

Workup

  1. temperatureThe reaction mixture was heated at 120° for 5 hrs
  2. temperaturere-heated to 120°-30° for 31/2 hrs
  3. temperatureThe mixture was then cooled to 70°
  4. temperaturecooled to room temperature
  5. extractionextracted with CHCl3
  6. washThey were washed three times with water
  7. dry with materialonce with saturated NaCl solution, dried over MgSO4
  8. filtrationfiltered
  9. additiontreated with charcoal
  10. filtrationfiltered through diatomaceous earth
  11. customthe solvent was removed in vacuo
  12. customto give a brown oil which
  13. distillationdistilled

Sources & evidence

ORD record
ord-10466fa59aa84a0d9711b02d5556c4a4
Source dataset
uspto-grants-1989_08
Patent number
US04861798

Reaction notes

Loading…