Hydrochloric Acid → HCID 13645764, compound

HRID 1982200Notes

Reaction equation

HRID 1982200 reaction equation
[CH3:1][N:2]([CH3:24])[CH2:3][CH2:4][CH2:5][C:6]1([C:19]([O:21]CC)=[O:20])[CH2:11][CH2:10][CH2:9][CH2:8][C:7]1([OH:18])[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.Cl>CCCCO.[OH-].[K+]>[CH3:24][N:2]([CH3:1])[CH2:3][CH2:4][CH2:5][C:6]1([C:19]([OH:21])=[O:20])[CH2:11][CH2:10][CH2:9][CH2:8][C:7]1([OH:18])[C:12]1[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 13645765HCID 13645765, compound

Product 1

HCID 13645764HCID 13645764, compound

Reagents, catalysts & solvents 2

HCID 2631-ButanolSolventHCID 14797Potassium HydroxideSolvent

Procedure

The ester from Example 2 (9.6 gm) in a mixture of 135 ml n-BuOH and 45 ml 45% KOH (aq) was refluxed with good stirring for 75 min., allowed to cool, and acidified with 68 ml conc. HCl. The reaction mixture was transferred to a 1 liter round bottom flask, rinsing and diluting with 40 ml n-BuOH. The mixture was concentrated to about 350 ml, cooled, and the KCl filtered off. The filtrate was concentrated to dryness then warmed and shaken with 40 ml acetonitrile, filtered and rinsed with acetonitrile (5 ml). The filtrate was cooled, seeded and the product allowed to crystallize. Wgt.=4.1 gm, m.p.=144°-145°. A second crop was obtained from the filtrate, Wgt.=1.1 gm.

Workup

  1. temperaturewas refluxed
  2. temperatureto cool
  3. customThe reaction mixture was transferred to a 1 liter round bottom flask
  4. washrinsing
  5. additiondiluting with 40 ml n-BuOH
  6. concentrationThe mixture was concentrated to about 350 ml
  7. temperaturecooled
  8. filtrationthe KCl filtered off
  9. concentrationThe filtrate was concentrated to dryness
  10. temperaturethen warmed
  11. stirringshaken with 40 ml acetonitrile
  12. filtrationfiltered
  13. washrinsed with acetonitrile (5 ml)
  14. temperatureThe filtrate was cooled
  15. customto crystallize
  16. customA second crop was obtained from the filtrate, Wgt

Sources & evidence

ORD record
ord-f13da148f3554c49b0538f96cdf600fa
Source dataset
uspto-grants-1986_06
Patent number
US04595759

Reaction notes

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