2-Hydroxyethyl-7-nitro-1,2,3,4-tetrahydroisoquinoline hydrochloride → 1-(2-Hydroxyethyl)-1,2,3,4-tetrahydroisoquinolin-7-amine hydrochloride

HRID 583240Notes

Reaction equation

HRID 583240 reaction equation
[ClH:1].[OH:2][CH2:3][CH2:4][CH:5]1[C:14]2[C:9](=[CH:10][CH:11]=[C:12]([N+:15]([O-])=O)[CH:13]=2)[CH2:8][CH2:7][NH:6]1>C(O)C.[Pd]>[ClH:1].[OH:2][CH2:3][CH2:4][CH:5]1[C:14]2[C:9](=[CH:10][CH:11]=[C:12]([NH2:15])[CH:13]=2)[CH2:8][CH2:7][NH:6]1

Participants

4

Reactant 1

HCID 215842782-Hydroxyethyl-7-nitro-1,2,3,4-tetrahydroisoquinoline hydrochloride

Product 1

HCID 215843191-(2-Hydroxyethyl)-1,2,3,4-tetrahydroisoquinolin-7-amine hydrochlorideYield 94%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

To a solution of 1-(2-hydroxyethyl)-7-nitro-1,2,3,4-tetrahydroisoquinoline hydrochloride (2.18 g, 8.43 mmol) in ethanol (100 ml) was added 10% Pd-C (0.4 g) and the solution hydrogenated on the Parr Hydrogenator for 2 h. The reaction mixture was filtered to remove the catalyst and the filtrate reduced to about 1/3 of the volume. The solution was warmed and ether (150 ml) was added. The precipitate was collected to give the title compound as a yellow solid (1.81 g, 94%), mp. 199.5-200.5° C.

Workup

  1. filtrationThe reaction mixture was filtered
  2. customto remove the catalyst
  3. temperatureThe solution was warmed
  4. additionether (150 ml) was added
  5. customThe precipitate was collected

Sources & evidence

ORD record
ord-73b9233396164cbab13f01b42fd1eef6
Source dataset
uspto-grants-1999_07
Patent number
US05929085

Reaction notes

Loading…