Sodium Hydroxide → HCID 22132530, compound

HRID 1856792Notes

Reaction equation

HRID 1856792 reaction equation
COC([N:5]1[CH2:14][CH2:13][C:12]2[C:7](=[CH:8][C:9]([CH2:15][S:16]([C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)(=[O:18])=[O:17])=[CH:10][CH:11]=2)[CH2:6]1)=O.[OH-].[Na+]>CO>[C:19]1([S:16]([CH2:15][C:9]2[CH:8]=[C:7]3[C:12]([CH2:13][CH2:14][NH:5][CH2:6]3)=[CH:11][CH:10]=2)(=[O:18])=[O:17])[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 22132512HCID 22132512, compound

Product 1

HCID 22132530HCID 22132530, compoundYield 99.3%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of 2-methoxycarbonyl-7-phenylsulfonylmethyl-1,2,3,4-tetrahydroisoquinoline (21.5 g, 6.2 mmol), sodium hydroxide (20 g, 0.5 mol) and methanol (250 ml) was heated at reflux for 64 h. The mixture was cooled and evaporation in vacuo, then the residue was partitioned between water (100 ml) and dichloromethane (5×50 ml). Combined organic extracts were dried (Na2SO4) and evaporated in vacuo to give the title compound as a colourless solid (1.77 g, 99%).

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 64 h
  3. temperatureThe mixture was cooled
  4. customevaporation in vacuo
  5. customthe residue was partitioned between water (100 ml) and dichloromethane (5×50 ml)
  6. dry with materialCombined organic extracts were dried (Na2SO4)
  7. customevaporated in vacuo

Sources & evidence

ORD record
ord-b52691d60b3746c7a6f229beb4d653b9
Source dataset
uspto-grants-2000_11
Patent number
US06143762

Reaction notes

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