Hydrochloric Acid → HCID 18958350, compound

HRID 2379297Notes

Reaction equation

HRID 2379297 reaction equation
C1(=O)[N:5]([CH2:6][CH2:7][CH2:8][CH2:9][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][CH2:24][CH2:25][CH2:26][C:27]([O:29]C)=[O:28])C(=O)C2=CC=CC=C12.O.NN.Cl>C(O)C>[NH2:5][CH2:6][CH2:7][CH2:8][CH2:9][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][CH2:24][CH2:25][CH2:26][C:27]([OH:29])=[O:28]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 24654Hydrazine hydrate (1:1)HCID 18958341HCID 18958341, compound

Product 1

HCID 18958350HCID 18958350, compoundYield 77.5%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of methyl 22-phthalimidodocosanoate (1.5 g, 3.0 mmoles), 40 ml of ethanol and 80% hydrazine hydrate was refluxed for 10 hours. To the reaction mixture was added 11.3 ml of 6N aqueous hydrochloric acid solution, and further refluxed for 1 hour. After removal by filtration of the insoluble matter that formed, the reaction mixture was concentrated under reduced pressure. To the residue were added 30 ml of ethanol and 15 ml of 1N aqueous sodium hydroxide solution, and the resulting mixture was refluxed for 19 hours. After neutralization of the reaction mixture with 6N aqueous hydrochloric acid solution, the precipitates that formed were collected by filtration and recrystallized from ethanol-acetic acid-water to give 22-aminodocosanoic acid (827 mg, 77%) having the following properties.

Workup

  1. temperaturewas refluxed for 10 hours
  2. temperaturefurther refluxed for 1 hour
  3. customAfter removal
  4. filtrationby filtration of the insoluble matter
  5. customthat formed
  6. concentrationthe reaction mixture was concentrated under reduced pressure
  7. additionTo the residue were added 30 ml of ethanol and 15 ml of 1N aqueous sodium hydroxide solution
  8. temperaturethe resulting mixture was refluxed for 19 hours
  9. customAfter neutralization of the reaction mixture with 6N aqueous hydrochloric acid solution, the precipitates
  10. customthat formed
  11. filtrationwere collected by filtration
  12. customrecrystallized from ethanol-acetic acid-water

Sources & evidence

ORD record
ord-6e1cf5dcdcd64bc28615194f435c0876
Source dataset
uspto-grants-1994_11
Patent number
US05360914

Reaction notes

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