Nitric Acid → 1(2H)-Isoquinolinone,7-amino-3,4-dihydro-2-methyl-(9CI)

HRID 905672Notes

Reaction equation

HRID 905672 reaction equation
[CH3:1][N:2]1[CH:11]=[CH:10][C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3]1=[O:12].[H][H].[N+:15]([O-])(O)=O>C(O)C.S(=O)(=O)(O)O.[Pd]>[NH2:15][C:6]1[CH:5]=[C:4]2[C:9]([CH2:10][CH2:11][N:2]([CH3:1])[C:3]2=[O:12])=[CH:8][CH:7]=1

Participants

7

Reactant 3

HCID 944Nitric AcidHCID 783431(2H)-Isoquinolinone, 2-methyl-HCID 178418361HCID 178418361, compound

Product 1

HCID 230715821(2H)-Isoquinolinone,7-amino-3,4-dihydro-2-methyl-(9CI)

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 702EthanolSolventHCID 1118Sulfuric AcidSolvent

Procedure

2-Methyl-2H-isoquinolin-1-one was subjected to catalytic hydrogenation in a hydrogen atmosphere in ethanol in the presence of palladium/carbon. The resulting compound and concentrated nitric acid were allowed to undergo the reaction in concentrated sulfuric acid. The resulting compound was subjected to catalytic hydrogenation in the same manner as shown in Reference Example 3 to obtain 7-amino-2-methyl-3,4-dihydro-2H-isoquinolin-1-one. NMR2: 2.88 (2 H, t, J=6.8 Hz), 3.13 (3 H, s), 6.95 (1 H, d, J=8.0 Hz).

Sources & evidence

ORD record
ord-3aea80a7b10a43c5b79c6fe2e6ae1fb9
Source dataset
uspto-grants-2011_09
Patent number
US08012959B2

Reaction notes

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