Hydrochloric Acid → 2-Hydroxyethyl-7-nitro-1,2,3,4-tetrahydroisoquinoline hydrochloride

HRID 369961Notes

Reaction equation

HRID 369961 reaction equation
[ClH:1].[N+:2]([C:5]1[CH:14]=[C:13]2[C:8]([CH2:9][CH2:10][NH:11][CH2:12]2)=[CH:7][CH:6]=1)([O-:4])=[O:3].[OH-].[Na+].[CH2:17]1[O:19][CH2:18]1.Cl>C(O)C>[ClH:1].[OH:19][CH2:18][CH2:17][CH:12]1[C:13]2[C:8](=[CH:7][CH:6]=[C:5]([N+:2]([O-:4])=[O:3])[CH:14]=2)[CH2:9][CH2:10][NH:11]1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 6354Ethylene OxideHCID 14798Sodium HydroxideHCID 135216707-Nitro-1,2,3,4-tetrahydroisoquinoline hydrochloride

Product 1

HCID 215842782-Hydroxyethyl-7-nitro-1,2,3,4-tetrahydroisoquinoline hydrochlorideYield 62%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent3×

Procedure

To a solution of 7-nitro-1,2,3,4-tetrahydroisoquinoline hydrochloride (5.01 g, 23.3 mmol) in ethanol (200 ml) at 0° C. in a pressure bottle was added 2.5 M sodium hydroxide solution (10 ml). This solution was stirred for 0.2 h before ethylene oxide (4.2 ml) was added and the bottle was capped and the solution was stirred overnight while slowly allowing it to warm to ambient temperature. The solvent was concentrated and the aqueous solution was extracted twice with dichloromethane. The combined and dried (magnesium sulfate) extracts were concentrated to give an oil. This oil was immediately dissolved in ethanol (125 ml) and hydrochloric acid in ethanol was added until a distinctly acidic solution was obtained. After cooling, the title compound was collected and isolated as an off-white solid (3.76 g, 62%), m.p. 213° C. (dec.).

Workup

  1. additionwas added
  2. customthe bottle was capped
  3. concentrationThe solvent was concentrated
  4. extractionthe aqueous solution was extracted twice with dichloromethane
  5. dry with materialdried (magnesium sulfate) extracts
  6. concentrationwere concentrated
  7. customto give an oil
  8. customwas obtained
  9. temperatureAfter cooling
  10. customthe title compound was collected

Sources & evidence

ORD record
ord-73a83ae02d634baa96960dccd5aa2e44
Source dataset
uspto-grants-2000_10
Patent number
US06140322

Reaction notes

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