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

HRID 369939Notes

Reaction equation

HRID 369939 reaction equation
[N+:1]([C:4]1[CH:13]=[C:12]2[C:7]([CH2:8][CH2:9][NH:10][CH:11]2[CH2:14][C:15](O)=[O:16])=[CH:6][CH:5]=1)([O-:3])=[O:2].B.[ClH:19]>C1COCC1.C(O)C>[ClH:19].[OH:16][CH2:15][CH2:14][CH:11]1[C:12]2[C:7](=[CH:6][CH:5]=[C:4]([N+:1]([O-:3])=[O:2])[CH:13]=2)[CH2:8][CH2:9][NH:10]1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 6331Borane2×HCID 215842657-Nitro-1,2,3,4-tetrahydroisoquinoline-1-acetic acid

Product 1

HCID 215842782-Hydroxyethyl-7-nitro-1,2,3,4-tetrahydroisoquinoline hydrochlorideYield 84%

Reagents, catalysts & solvents 2

HCID 702EthanolSolvent2×HCID 8028TetrahydrofuranSolvent2×

Procedure

To a suspension of 7-nitro-1,2,3,4-tetrahydroisoquinolin-1-acetic acid in anhydrous THF (20 ml) at 0° C. was added 1.0M borane in THF (25 ml). The reaction mixture was slowly warmed to ambient temperature and stirring was continued for 4 h. Since the reaction was not proceeding to completion, additional borane (10 ml) was added and the solution heated at reflux for 1 h. Upon cooling to ambient temperature, the reaction was quenched by the addition of methanol (1 ml) and 6M hydrochloric acid (5 ml). The solution was heated at reflux for 2 h to decompose any borate intermediates and the solvent concentrated at the rotoevaporator. The resulting oil was taken up in water, made basic with dilute NaOH, and extracted twice with dichloromethane. The dried (MgSO4) organic extracts were concentrated to give a solid. This solid was dissolved in hot ethanol (75 ml) and hydrochloric acid in ethanol added to give an acidic solution. The product was isolated by filtration of the precipitate to give the title compound as a light yellow solid (2.28 g, 84%), m.p. 238-40° C.

Workup

  1. additionwas added
  2. temperaturethe solution heated
  3. temperatureat reflux for 1 h
  4. temperatureUpon cooling to ambient temperature
  5. customthe reaction was quenched by the addition of methanol (1 ml) and 6M hydrochloric acid (5 ml)
  6. temperatureThe solution was heated
  7. temperatureat reflux for 2 h
  8. concentrationthe solvent concentrated at the rotoevaporator
  9. extractionextracted twice with dichloromethane
  10. dry with materialThe dried (MgSO4) organic extracts
  11. concentrationwere concentrated
  12. customto give a solid
  13. customto give an acidic solution
  14. customThe product was isolated by filtration of the precipitate

Sources & evidence

ORD record
ord-a4c7b2d6ebae49b7bdcc6267911c4acf
Source dataset
uspto-grants-2000_10
Patent number
US06140322

Reaction notes

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