Ammonium Chloride → HCID 68521214, compound

HRID 522852Notes

Reaction equation

HRID 522852 reaction equation
[CH:1]1([C:4]2[CH:5]=[C:6]3[C:11](=[CH:12][CH:13]=2)[CH:10]=[N:9][CH:8]=[CH:7]3)[CH2:3][CH2:2]1.[In].[NH4+].[Cl-]>CCO>[CH:1]1([C:4]2[CH:5]=[C:6]3[C:11](=[CH:12][CH:13]=2)[CH2:10][NH:9][CH2:8][CH2:7]3)[CH2:3][CH2:2]1

Participants

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 5359967IndiumHCID 67355115HCID 67355115, compound

Product 1

HCID 68521214HCID 68521214, compoundYield 58%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 6-cyclopropylisoquinoline (0.500 g, 0.003 mol) in EtOH (15 mL) was added indium powder (3 g) and saturated aqueous NH4Cl (5 mL). The reaction mixture was heated at reflux for 36 h while stirring. After completion, the reaction mixture was filtered through Celite® (diatomaceous earth) and the filtrate concentrated at reduced pressure to afford crude 6-cyclopropyl-1,2,3,4-tetrahydro-isoquinoline. Purification was done by silica gel column chromatography eluting with MeOH in CH2Cl2 (0-10%) to afford pure 6-cyclopropyl-1,2,3,4-tetrahydro-isoquinoline (0.300 g, 58%) as a white solid.

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureat reflux for 36 h
  3. filtrationAfter completion, the reaction mixture was filtered through Celite® (diatomaceous earth)
  4. concentrationthe filtrate concentrated at reduced pressure
  5. customto afford crude 6-cyclopropyl-1,2,3,4-tetrahydro-isoquinoline
  6. customPurification
  7. washeluting with MeOH in CH2Cl2 (0-10%)

Sources & evidence

ORD record
ord-fdf43fb32a1241deb4c5580d4a57d6d9
Source dataset
uspto-grants-2016_05
Patent number
US09334269B2

Reaction notes

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