Hydrochloric Acid → HCID 45261558, compound

HRID 1460668Notes

Reaction equation

HRID 1460668 reaction equation
Cl.FC1[CH:4]=[C:5]([C:9]([C:23]2[CH:28]=[CH:27][CH:26]=[C:25](F)[CH:24]=2)=[CH:10][O:11][CH2:12][CH2:13][N:14]2[CH2:19][CH2:18][CH:17]=[C:16]([C:20]([OH:22])=[O:21])[CH2:15]2)[CH:6]=[CH:7][CH:8]=1.[OH-].[Na+].Cl.[Cl:33][CH2:34][Cl:35].[CH2:36](O)C>>[ClH:33].[Cl:35][C:34]1[CH:4]=[C:5](/[C:9](/[C:23]2[CH:24]=[CH:25][CH:26]=[CH:27][C:28]=2[CH3:36])=[CH:10]/[O:11][CH2:12][CH2:13][N:14]2[CH2:19][CH2:18][CH:17]=[C:16]([C:20]([OH:22])=[O:21])[CH2:15]2)[CH:6]=[CH:7][CH:8]=1

Participants

6

Reactant 5

HCID 313Hydrochloric AcidHCID 702EthanolHCID 6344DichloromethaneHCID 14798Sodium HydroxideHCID 45264923HCID 45264923, compound

Product 1

HCID 45261558HCID 45261558, compoundYield 30%

Procedure

E or Z-1-[2-[[2-(3-Chlorophenyl)-2-(2-methylphenyl)ethenyl]oxy]ethyl]-1,2,5,6-tetrahydro-3-pyridine carboxylic acid methyl ester (0.55 g, 0.0013 mol) (prepared as described in Method D) was dissolved in ethanol (5 ml) and 12N 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 the pH was measured as ca. 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, m.p. 214°-215°.

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-8869a0e13dee4312a82c609d6c89610e
Source dataset
uspto-grants-1991_12
Patent number
US05071859

Reaction notes

Loading…