Ammonium Acetate → 6-Amino-2-N-Boc-1,2,3,4-tetrahydro-isoquinoline

HRID 1954415Notes

Reaction equation

HRID 1954415 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:17][CH2:16][C:15]2[C:10](=[CH:11][C:12](Br)=[C:13]([N+:18]([O-])=O)[CH:14]=2)[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].C([O-])(=O)C.[NH4+]>C(O)(=O)C.[Pd]>[C:1]([O:5][C:6]([N:8]1[CH2:17][CH2:16][C:15]2[C:10](=[CH:11][CH:12]=[C:13]([NH2:18])[CH:14]=2)[CH2:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 2

HCID 517165Ammonium AcetateHCID 542872931,1-Dimethylethyl 7-bromo-3,4-dihydro-6-nitro-2(1H)-isoquinolinecarboxylate

Product 1

HCID 27563716-Amino-2-N-Boc-1,2,3,4-tetrahydro-isoquinolineYield 100.7%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 176Acetic AcidSolvent

Procedure

A total of 59 g (0.16 mol) of 7-bromo-6-nitro-3,4-dihydro-1H-isoquinoline-2-carboxylic acid tert-butyl ester, 10 g of 5% palladium on calcium carbonate and 49 g of ammonium acetate in 1 liter of acetic acid was hydrogenated on a Parr shaker for 5 hrs. The reaction was filtered, concentrated, basified to pH 12 with 4N sodium hydroxide and extracted with methylene chloride. The organic layer was washed with water and brine, dried over magnesium sulfate and concentrated to yield 40 g of the title compound in the form of an oil.

Workup

  1. filtrationThe reaction was filtered
  2. concentrationconcentrated
  3. extractionextracted with methylene chloride
  4. washThe organic layer was washed with water and brine
  5. dry with materialdried over magnesium sulfate
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-0a1da14fc57b4acc900fab6497e512f2
Source dataset
uspto-grants-2000_09
Patent number
US06121283

Reaction notes

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