Hydrochloric Acid → HCID 178470910, compound

HRID 1049516Notes

Reaction equation

HRID 1049516 reaction equation
[CH:1]1([CH:4]([C:11]2[CH:16]=[CH:15][CH:14]=[C:13]([CH2:17][O:18][C:19]3[CH:20]=[N:21][C:22]([O:30]C)=[C:23]([CH2:25][C:26]([CH3:29])([CH3:28])[CH3:27])[CH:24]=3)[CH:12]=2)[CH2:5][C:6]([O:8][CH2:9][CH3:10])=[O:7])[CH2:3][CH2:2]1.[Cl-].[NH+]1C=CC=CC=1.Cl>CN(C=O)C>[CH:1]1([CH:4]([C:11]2[CH:16]=[CH:15][CH:14]=[C:13]([CH2:17][O:18][C:19]3[CH:20]=[N:21][C:22]([OH:30])=[C:23]([CH2:25][C:26]([CH3:29])([CH3:28])[CH3:27])[CH:24]=3)[CH:12]=2)[CH2:5][C:6]([O:8][CH2:9][CH3:10])=[O:7])[CH2:3][CH2:2]1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 69401Einecs 211-027-4HCID 117759589HCID 117759589, compound

Product 1

HCID 178470910HCID 178470910, compoundYield 8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

To a solution of ethyl 3-cyclopropyl-3-(3-(((6-methoxy-5-neopentylpyridin-3-yl)oxy)methyl)phenyl)propanoate (2.86 g) in DMF (20 mL) was added pyridinium chloride (7.77 g), and the mixture was stirred at 100° C. for 3 hr. To the reaction mixture was added 1N hydrochloric acid (100 mL), and the mixture was extracted with ethyl acetate. The extract was washed with saturated brine, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure, and the obtained residue was crystallized from diisopropyl ether to give the title compound (220 mg) as white crystals.

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe extract was washed with saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customThe solvent was evaporated under reduced pressure
  5. customthe obtained residue was crystallized from diisopropyl ether

Sources & evidence

ORD record
ord-ee8a0bd3d7e3422da4fc8a1537467bf6
Source dataset
uspto-grants-2016_07
Patent number
US09382188B2

Reaction notes

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