Hydrochloric Acid → HCID 70230442, compound

HRID 566575Notes

Reaction equation

HRID 566575 reaction equation
C[O:2][C:3]([C:5]1[CH2:6][N:7]([CH2:11][CH2:12][O:13]/[CH:14]=[C:15](/[C:23]2[CH:28]=[CH:27][CH:26]=[C:25]([Cl:29])[CH:24]=2)\[C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=2[CH3:22])[CH2:8][CH2:9][CH:10]=1)=[O:4].[OH-].[Na+].Cl.ClCCl>C(O)C>[ClH:29].[Cl:29][C:25]1[CH:24]=[C:23]([C:15]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=2[CH3:22])=[CH:14][O:13][CH2:12][CH2:11][N:7]2[CH2:8][CH2:9][CH:10]=[C:5]([C:3]([OH:4])=[O:2])[CH2:6]2)[CH:28]=[CH:27][CH:26]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 6344DichloromethaneHCID 14798Sodium HydroxideHCID 70231147HCID 70231147, compound

Product 1

HCID 70230442HCID 70230442, compoundYield 30%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

E or Z-1-(2-((2-(3-Chlorophenyl)-2-(2-methylphenyl)ethenyl)oxy)ethyl)-1,2,5,6-tetrahydro-3-pyridinecarboxylic acid methyl ester (0.55 g, 0.0013 mol, prepared similarly to the method described in Example 70) was dissolved in ethanol (5 ml) and 12 N sodium hydroxide solution (0.33 ml) was introduced. After stirring the solution at room temperature for 3 h, 37% hydrochloric acid solution was added until pH 1. Dichloromethane (200 ml) was introduced, and the mixture was dried (Na2SO4), filtered and evaporated to a residue, which was co-evaporated twice with acetone. Recrystallization from acetone/ethyl acetate provided the title compound (0.17 g, 30%) as a white solid.

Workup

  1. dry with materialthe mixture was dried (Na2SO4)
  2. filtrationfiltered
  3. customevaporated to a residue, which
  4. customRecrystallization from acetone/ethyl acetate

Sources & evidence

ORD record
ord-c15eb15df4d542dcbde5af7427da2c72
Source dataset
uspto-grants-2001_01
Patent number
US06174898B1

Reaction notes

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