Hydrochloric Acid → HCID 10406292, compound

HRID 2380328Notes

Reaction equation

HRID 2380328 reaction equation
[C:1]1([C:7]2[CH:12]=[C:11]([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=3)[N:10]=[C:9]([O:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][C:25]([O:27]CC)=[O:26])[CH:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[OH-].[Na+].Cl>C(O)C.O>[C:1]1([C:7]2[CH:12]=[C:11]([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=3)[N:10]=[C:9]([O:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][C:25]([OH:27])=[O:26])[CH:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 10408018HCID 10408018, compound

Product 1

HCID 10406292HCID 10406292, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

To a solution of ethyl 6-[(4,6-diphenyl-2-pyridyl)oxy]hexanoate (3.7 g) in ethanol (100 cc) are added sodium hydroxide pellets (0.6 g). The reaction mixture is refluxed for 1 hour and then concentrated to dryness under reduced pressure. The residue obtained is dissolved in distilled water (150 cc). The pH of the aqueous phase is brought to about 5 by addition of a 2N aqueous solution of hydrochloric acid. It is then extracted with methylene chloride (3×50 cc). The organic phases are combined, washed with distilled water (3×50 cc), dried over sodium sulphate and concentrated to dryness at 40° C. under reduced pressure. The solid residue obtained is purified by recrystallization in an n-hexane-ethyl acetate (10-1) mixture (55 cc). (white crystals; m.p.=87°-88° C.)

Workup

  1. temperatureThe reaction mixture is refluxed for 1 hour
  2. concentrationconcentrated to dryness under reduced pressure
  3. customThe residue obtained
  4. extractionIt is then extracted with methylene chloride (3×50 cc)
  5. washwashed with distilled water (3×50 cc)
  6. dry with materialdried over sodium sulphate
  7. concentrationconcentrated to dryness at 40° C. under reduced pressure
  8. customThe solid residue obtained
  9. customis purified by recrystallization in an n-hexane-ethyl acetate (10-1) mixture (55 cc)

Sources & evidence

ORD record
ord-06ea4853f32f432da24ac8a941e96e45
Source dataset
uspto-grants-1994_11
Patent number
US05366982

Reaction notes

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