Chloral Hydrate → N-(5-Bromo-1,2,3,4-tetrahydro-2-methylisoquinolin-8-yl)-2-(hydroxyimino)acetamide

HRID 2237386Notes

Reaction equation

HRID 2237386 reaction equation
[Br:1][C:2]1[CH:11]=[CH:10][C:9]([NH2:12])=[C:8]2[C:3]=1[CH2:4][CH2:5][N:6]([CH3:13])[CH2:7]2.Cl[C:15](Cl)(Cl)[CH:16]([OH:18])O.Cl.[NH2:22][OH:23].[O-]S([O-])(=O)=O.[Na+].[Na+].[OH-].[Na+]>O.CCO>[Br:1][C:2]1[CH:11]=[CH:10][C:9]([NH:12][C:16](=[O:18])[CH:15]=[N:22][OH:23])=[C:8]2[C:3]=1[CH2:4][CH2:5][N:6]([CH3:13])[CH2:7]2

Participants

7

Reactant 5

HCID 2707Chloral HydrateHCID 14798Sodium HydroxideHCID 24436Sodium SulfateHCID 443297Hydroxyamine hydrochlorideHCID 99919145-Bromo-2-methyl-1,2,3,4-tetrahydroisoquinolin-8-amine

Product 1

HCID 76727667N-(5-Bromo-1,2,3,4-tetrahydro-2-methylisoquinolin-8-yl)-2-(hydroxyimino)acetamide

Reagents, catalysts & solvents 1

HCID 19096565Water ethanolSolvent

Conditions

Temperature
60 °C

Procedure

A mixture of 5-bromo-1,2,3,4-tetrahydro-2-methylisoquinolin-8-amine (IV, 3.25 g, 13.5 mmol), chloral hydrate (2.3 g), hydroxylamine hydrochloride (2.9 g), 12 g Na2SO4 (12 g) in H2O:EtOH (3:1, 50 mL) was refluxed for 1 hr whereafter it was cooled to 60° C. and carefully basified with 4N NaOH to pH=7 and allowed to cool. The solid was collected by filtration, washed with water and dried under vacuum to give V.

Workup

  1. temperaturewas refluxed for 1 hr whereafter it
  2. temperatureto cool
  3. filtrationThe solid was collected by filtration
  4. washwashed with water
  5. customdried under vacuum
  6. customto give V

Sources & evidence

ORD record
ord-c3094fffd10640f9bc955905f84120a6
Source dataset
uspto-grants-2010_05
Patent number
US07718641B2

Reaction notes

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