Water → HCID 21271722, compound

HRID 1194109Notes

Reaction equation

HRID 1194109 reaction equation
[C:1]1([S:7]([NH:10][C:11]2[CH:12]=[C:13]3[C:18](=[CH:19][CH:20]=2)[CH:17]=[N:16][CH:15]=[CH:14]3)(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[H][H].O>C(O)(=O)C.[Pt]=O>[C:1]1([S:7]([NH:10][C:11]2[CH:12]=[C:13]3[C:18](=[CH:19][CH:20]=2)[CH2:17][NH:16][CH2:15][CH2:14]3)(=[O:9])=[O:8])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

6

Reactant 3

HCID 962WaterHCID 3602611HCID 3602611, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 21271722HCID 21271722, compoundYield 76.2%

Reagents, catalysts & solvents 2

HCID 82844Platinum oxide (PtO)CatalystHCID 176Acetic AcidSolvent

Procedure

A solution of 6-phenylsulphonamidoisoquinoline (2.11 g, 0.0074M) in acetic acid (50 ml) was hydrogenated over a platinum oxide catayst (0.5 g) at approximately 345 kilopascals pressure and room temperature for 3 hours (the theoretical uptake of hydrogen was observed). A small volume of H2O was added to dissolve the product and the catalyst was then filtered off. The filtrate was evaporated to dryness to yield an oil which crystallised under ether to yield 6-phenylsulphonamido-1,2,3,4-tetrahydroisoquinoline (1.63 g, 76%).

Workup

  1. dissolutionto dissolve the product
  2. filtrationthe catalyst was then filtered off
  3. customThe filtrate was evaporated to dryness
  4. customto yield an oil which
  5. customcrystallised under ether

Sources & evidence

ORD record
ord-f4e7a0367ea44113b5adcd09fa115acb
Source dataset
uspto-grants-1989_03
Patent number
US04812573

Reaction notes

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