Acetic Acid → HCID 13017865, compound

HRID 444282Notes

Reaction equation

HRID 444282 reaction equation
[ClH:1].CO[N:4]=[C:5]1[CH2:24][CH2:23][C:8]2([C:16]3[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=3)[CH:10]([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)[O:9]2)[CH2:7][CH2:6]1.C(O)(=O)C.[H][H].Cl.CCOCC>CCOCC>[ClH:1].[NH2:4][CH:5]1[CH2:6][CH2:7][C:8]2([C:16]3[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=3)[CH:10]([CH:17]3[CH2:22][CH2:21][CH2:20][CH2:19][CH2:18]3)[O:9]2)[CH2:23][CH2:24]1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 10953452Ether hydrochlorideHCID 20562140HCID 20562140, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 13017865HCID 13017865, compoundYield 66%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

A mixture of 1.50 of 4-methoxyimino-3'-phenylspiro[cyclohexane-1,1'(3'H)-isobenzofuran]hydrochloride, 150 ml of acetic acid and 0.5 g of platinujm oxide is hydrogen at 50 psi and room temperature for 41/2 hours. After filtration and removing the solvent, the oily product is dissolved in 100 ml of dichloromethane and washed with 5% sodium hydroxide solution and water. After drying over anhydrous sodium sulfate, the solvent is removed in vacuo to give an oil. The oil is dissolved in 10 ml of methaol and the solution is made acidic using hydrogen chloride/ether. After addition of 50 ml of ether, the preceipitate is suction filtered, washed with ether and dried to give 66.0% of product, mp 220°-224° C.

Workup

  1. customat 50 psi and room temperature
  2. custom2 hours
  3. filtrationAfter filtration
  4. customremoving the solvent
  5. dissolutionthe oily product is dissolved in 100 ml of dichloromethane
  6. washwashed with 5% sodium hydroxide solution and water
  7. dry with materialAfter drying over anhydrous sodium sulfate
  8. customthe solvent is removed in vacuo
  9. customto give an oil
  10. dissolutionThe oil is dissolved in 10 ml of methaol
  11. filtrationfiltered
  12. washwashed with ether
  13. customdried

Sources & evidence

ORD record
ord-b3c8d12a79784366b8bde60044b18063
Source dataset
uspto-grants-1981_04
Patent number
US04263317

Reaction notes

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