Hydrochloric Acid → HCID 45377689, compound

HRID 1184527Notes

Reaction equation

HRID 1184527 reaction equation
Cl.Cl.[Cl:3][C:4]1[C:9]([O:10][CH2:11][C:12]2[CH:17]=[CH:16][N:15]=[CH:14][CH:13]=2)=[CH:8][CH:7]=[CH:6][C:5]=1[NH:18][C:19](=[O:34])/[CH:20]=[CH:21]/[C:22]1[CH:27]=[CH:26][C:25]([O:28][CH3:29])=[C:24]([O:30]C(=O)C)[CH:23]=1>C1COCC1>[ClH:3].[Cl:3][C:4]1[C:9]([O:10][CH2:11][C:12]2[CH:17]=[CH:16][N:15]=[CH:14][CH:13]=2)=[CH:8][CH:7]=[CH:6][C:5]=1[NH:18][C:19](=[O:34])/[CH:20]=[CH:21]/[C:22]1[CH:27]=[CH:26][C:25]([O:28][CH3:29])=[C:24]([OH:30])[CH:23]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 67338717HCID 67338717, compound

Product 1

HCID 45377689HCID 45377689, compoundYield 195.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A 3N methanolic solution of hydrochloric acid (10 ml, 30 mmols) is added to a solution of (E)-N-[2-chloro-3-(pyridin-4-ylmethoxy)-phenyl]-3-(3-acetoxy-4-methoxy-phenyl)-acrylamide hydrochloride (240 mg, 0.53 mmol) in THF (5 mL). The resulting mixture was stirred at RT for 16 hrs, concentrated under reduced pressure, taken up with solvent an re-evaporated (3 times with MeOH and once with acetone) to give a light yellow residue that was triturated with ethyl ether. After filtration and drying, 232 mg of the title (E)-N-[2-chloro-3-(pyridin-4-ylmethoxy)-phenyl]-3-(3-hydroxy-4-methoxy-phenyl)-acrylamide hydrochloride were obtained as a light yellow powder.

Workup

  1. concentrationconcentrated under reduced pressure
  2. customan re-evaporated (3 times with MeOH
  3. customonce with acetone) to give a light yellow residue that
  4. customwas triturated with ethyl ether
  5. filtrationAfter filtration
  6. customdrying

Sources & evidence

ORD record
ord-efb933911a394e01834bde3c68f204ff
Source dataset
uspto-grants-2014_03
Patent number
US08669261B2

Reaction notes

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