Ammonium formate → 7-Amino-4,4-dimethyl-3,4-dihydroisoquinolin-1(2h)-one

HRID 1947646Notes

Reaction equation

HRID 1947646 reaction equation
[CH3:1][C:2]1([CH3:16])[C:11]2[C:6](=[CH:7][C:8]([N+:12]([O-])=O)=[CH:9][CH:10]=2)[C:5](=[O:15])[NH:4][CH2:3]1.C([O-])=O.[NH4+]>CN(C=O)C.[Pd]>[NH2:12][C:8]1[CH:7]=[C:6]2[C:11]([C:2]([CH3:16])([CH3:1])[CH2:3][NH:4][C:5]2=[O:15])=[CH:10][CH:9]=1

Participants

5

Reactant 2

HCID 2723923Ammonium formateHCID 142099534,4-Dimethyl-7-nitro-3,4-dihydroisoquinolin-1(2H)-one

Product 1

HCID 219596427-Amino-4,4-dimethyl-3,4-dihydroisoquinolin-1(2h)-oneYield 98%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 6228DimethylformamideSolvent

Procedure

Palladium/Carbon (10% wt) (25 mg, 0.13 mmol) was added to a stirred solution of 4,4-dimethyl-7-nitro-3,4-dihydro-2H-isoquinolin-1-one (250 mg, 1.13 mmol) and ammonium formate (350 mg, 5.65 mmol) in anhydrous DMF (10 ml) at room temperature. The resulting suspension was then heated at reflux for 1 hrs, then cooled and filtered through a pad of celite. The solvent was evaporated and the crude residue purified by flash column chromatography (5% methanol in dichloromethane) to afford the title compound as a pale yellow solid (210 mg, 98%). HPLC retention time 1.00 min. Mass spectrum (ES+) m/z 191 (M+H).

Workup

  1. temperatureThe resulting suspension was then heated
  2. temperatureat reflux for 1 hrs
  3. temperaturecooled
  4. filtrationfiltered through a pad of celite
  5. customThe solvent was evaporated
  6. customthe crude residue purified by flash column chromatography (5% methanol in dichloromethane)

Sources & evidence

ORD record
ord-81357852d1d54129b990020cffa1549c
Source dataset
uspto-grants-2013_03
Patent number
US08399481B2

Reaction notes

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