Hydrochloric Acid → HCID 18477217, compound

HRID 2379292Notes

Reaction equation

HRID 2379292 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][C:25]([O:27]C)=[O:26])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][C:25]([OH:27])=[O:26]

Participants

5

Reactant 3

HCID 313Hydrochloric Acid2×HCID 24654Hydrazine hydrate (1:1)HCID 18958344HCID 18958344, compound

Product 1

HCID 18477217HCID 18477217, compoundYield 72%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of methyl 20-phthalimidoeicosanoate (5.0 g, 10.6 mmoles), 100 ml of ethanol, 80% hydrazine hydrate (1.0 ml, 15.9 mmoles) was refluxed for 9 hours. After the addition of 26.5 ml of 6N aqueous hydrochloric acid, the reaction mixture was further refluxed for 1 hour. The insoluble matter that formed was removed by filtration. The liltrate was concentrated under reduced pressure. To the residue were added 70 ml of ethanol and 42.4 ml of 1N aqueous sodium hydroxide solution, and the obtained reaction mixture was refluxed for 16 hours. The reaction mixture was neutralized by adding 6N aqueous hydrochloric acid solution under ice-cooled condition. The precipitates that formed were collected by filtration and recrystallized from ethanolacetic acid-water, to give 20-aminoeicosanoic acid (2.50 g, 72%) having the following properties.

Workup

  1. temperaturewas refluxed for 9 hours
  2. temperaturethe reaction mixture was further refluxed for 1 hour
  3. customThe insoluble matter that formed
  4. customwas removed by filtration
  5. concentrationThe liltrate was concentrated under reduced pressure
  6. additionTo the residue were added 70 ml of ethanol and 42.4 ml of 1N aqueous sodium hydroxide solution
  7. customthe obtained reaction mixture
  8. temperaturewas refluxed for 16 hours
  9. temperaturecooled condition
  10. customThe precipitates
  11. customthat formed
  12. filtrationwere collected by filtration
  13. customrecrystallized from ethanolacetic acid-water

Sources & evidence

ORD record
ord-1387678d03274374a9fe33167721d66b
Source dataset
uspto-grants-1994_11
Patent number
US05360914

Reaction notes

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