Ethyl Acetate → 7-Amino-1,2,3,4-tetrahydroisoquinolin-1-one

HRID 1843899Notes

Reaction equation

HRID 1843899 reaction equation
[N+:1]([C:4]1[CH:13]=[C:12]2[C:7]([CH2:8][CH2:9][NH:10][C:11]2=[O:14])=[CH:6][CH:5]=1)([O-])=O.C(OC(=O)C)C>CO.[Pd]>[NH2:1][C:4]1[CH:13]=[C:12]2[C:7]([CH2:8][CH2:9][NH:10][C:11]2=[O:14])=[CH:6][CH:5]=1

Participants

5

Reactant 2

HCID 8857Ethyl AcetateHCID 131528427-Nitro-3,4-dihydroisoquinolin-1(2H)-one

Product 1

HCID 131528447-Amino-1,2,3,4-tetrahydroisoquinolin-1-oneYield 105.2%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

10% Pd/C (100 mg) was added to a solution of 7-nitro-3,4-dihydro-2H-isoquinolin-1-one (I-24a: 900 mg, 4.6875 mmol) in methanol (20 mL) at room temperature under nitrogen atmosphere. The resulting mixture was hydrogenated at room temperature for 3.5 hours. The reaction was monitored by TLC (100% ethylacetate). The reaction mixture was filtered; the filtrate was concentrated and dried to afford 800 mg of the crude product which was used in the next step without further purification.

Workup

  1. filtrationThe reaction mixture was filtered
  2. concentrationthe filtrate was concentrated
  3. customdried

Sources & evidence

ORD record
ord-873d1cef2d3d484f8724f38ec039c25a
Source dataset
uspto-grants-2015_02
Patent number
US08946260B2

Reaction notes

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