Sodium Hydroxide → HCID 85327164, compound

HRID 1268936Notes

Reaction equation

HRID 1268936 reaction equation
[Cl:1][C:2]1[CH:40]=[CH:39][C:5]([O:6][CH:7]([CH2:13][C:14]2[CH:19]=[CH:18][C:17]([O:20][CH2:21][CH2:22][O:23][N:24]=[C:25]([C:27]3[CH:32]=[CH:31][C:30]([C:33]4[CH:38]=[CH:37][CH:36]=[CH:35][N:34]=4)=[CH:29][CH:28]=3)[CH3:26])=[CH:16][CH:15]=2)[C:8]([O:10]CC)=[O:9])=[CH:4][CH:3]=1.[OH-].[Na+]>C(O)C>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([O:6][CH:7]([CH2:13][C:14]2[CH:15]=[CH:16][C:17]([O:20][CH2:21][CH2:22][O:23][N:24]=[C:25]([C:27]3[CH:32]=[CH:31][C:30]([C:33]4[CH:38]=[CH:37][CH:36]=[CH:35][N:34]=4)=[CH:29][CH:28]=3)[CH3:26])=[CH:18][CH:19]=2)[C:8]([OH:10])=[O:9])=[CH:39][CH:40]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 86591436HCID 86591436, compound

Product 1

HCID 85327164HCID 85327164, compoundYield 35.6%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of ethyl 2-(4-chlorophenoxy)-3-[4-[2-[[1-[4-(2-pyridyl)phenyl]ethylidene]aminoxy]ethoxy]phenyl]propionate (500 mg) obtained from Reference example 2 in ethanol (8 ml) was added an aqueous sodium hydroxide solution (1N, 1.79 ml), and the resulting solution was heated under reflux for 3 hours. The reaction solution was concentrated under reduced pressure, hydrochloric acid (1N) was added thereto to neutralize the solution, and then ethyl acetate was added thereto to extract the target compound. The separated organic layer was washed with a saturated aqueous sodium chloride solution, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The obtained crude product was purified by chromatography on a silica gel column (eluant; methylene chloride/methanol=9/1) to afford the target compound (169 mg) as a colorless foam.

Workup

  1. temperaturethe resulting solution was heated
  2. temperatureunder reflux for 3 hours
  3. concentrationThe reaction solution was concentrated under reduced pressure, hydrochloric acid (1N)
  4. additionwas added
  5. additionethyl acetate was added
  6. extractionto extract the target compound
  7. washThe separated organic layer was washed with a saturated aqueous sodium chloride solution
  8. dry with materialdried over anhydrous magnesium sulfate
  9. concentrationconcentrated under reduced pressure
  10. customThe obtained crude product
  11. customwas purified by chromatography on a silica gel column (eluant; methylene chloride/methanol=9/1)

Sources & evidence

ORD record
ord-a975134016934e9183274c03447c31f6
Source dataset
uspto-grants-2007_04
Patent number
US07199139B2

Reaction notes

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