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

HRID 580932Notes

Reaction equation

HRID 580932 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

59 g (0.16 mol) of 7-bromo-6-nitro-3,4-dihydro-1H-isoquinolin-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 through CELITE®concentrated, basified to pH 12 with 4N sodium hydroxide and extracted with methylene chloride. The organic layer was washed with water, brine, dried over magnesium sulfate and concentrated to yield 40 g of an oil.

Workup

  1. filtrationThe reaction was filtered through CELITE®concentrated
  2. extractionextracted with methylene chloride
  3. washThe organic layer was washed with water, brine
  4. dry with materialdried over magnesium sulfate
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-a1bad664e88d46c58a4f1c80a2b7b7e9
Source dataset
uspto-grants-1999_07
Patent number
US05919795

Reaction notes

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