Hydrochloric Acid → HCID 178471168, compound

HRID 2257008Notes

Reaction equation

HRID 2257008 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[C:11](=[O:12])[C:10]([CH:13]=[CH:14][C:15]([O:17][CH2:18][CH3:19])=[O:16])=[C:9]([O:20]C)[C:8](=[O:22])[NH:7][C:6]=2[CH:23]=1.O.[OH-].[Li+].Cl>O1CCCC1.O>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[C:11](=[O:12])[C:10](/[CH:13]=[CH:14]/[C:15]([O:17][CH2:18][CH3:19])=[O:16])=[C:9]([OH:20])[C:8](=[O:22])[NH:7][C:6]=2[CH:23]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 168937Lithium hydroxide, monohydrateHCID 541837368-Chloro-4-[2-(ethoxycarbonyl)ethenyl]-3-methoxy-2,5-dioxo-2,5-dihydro-1H-benz[b]azepine

Product 1

HCID 178471168HCID 178471168, compoundYield 83.1%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of 8-Chloro-4-[2-(ethoxycarbonyl)ethenyl]-3-methoxy-2,5-dioxo-2,5-dihydro-1H-benz[b]azepine (0.1009 g) in tetrahydrofuran (2.3 mL) was treated with a solution of lithium hydroxide monohydrate (0.0126 g) in tetrahydrofuran (2.3 mL) and water (0.5 mL) at room temperature. The solution was stirred at room temperature under argon for 68 hours. It was then added to 0.05N hydrochloric acid (10 mL). The resulting solid was filtered off, washed with water, and air-dried to give a light tan solid (0.0803 g). The solid was dissolved in hot ethanol (5 mL). The solution was filtered and treated with water (2 mL). The crystals were filtered off at room tempeature, washed with aqueous ethanol (1:1, v:v) and dried under vaccum to give a light tan solid (0.054 g); mp 177.5°-178.4° C.; 1H NMR (d6 -DMSO) 7.74 (d,1, J=16) 6.74 (d,1, J=16) for trans olefin protons; MS: m/z=276 (base peak), 322 (M+1). Analysis for C15H12ClNO5 : Calculated: C, 56.00; E, 3.78; N, 3.99; Found: C, 56.55; H, 3.78; N, 3.99.

Workup

  1. filtrationThe resulting solid was filtered off
  2. washwashed with water
  3. customair-dried

Sources & evidence

ORD record
ord-edf0953b7872449d86e939bddff416dc
Source dataset
uspto-grants-1997_08
Patent number
US05656626

Reaction notes

Loading…