3-Methyl-5-nitroisoquinoline → 3-Methylisoquinolin-5-amine

HRID 1911272Notes

Reaction equation

HRID 1911272 reaction equation
[CH3:1][C:2]1[N:3]=[CH:4][C:5]2[C:10]([CH:11]=1)=[C:9]([N+:12]([O-])=O)[CH:8]=[CH:7][CH:6]=2.[H][H]>C(O)C.C1COCC1.[Pd]>[CH3:1][C:2]1[N:3]=[CH:4][C:5]2[CH:6]=[CH:7][CH:8]=[C:9]([NH2:12])[C:10]=2[CH:11]=1

Participants

6

Reactant 2

HCID 2749733-Methyl-5-nitroisoquinolineHCID 178418361HCID 178418361, compound

Product 1

HCID 122120553-Methylisoquinolin-5-amineYield 94%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 702EthanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of Example 35A (1.60 g, 8.82 mmol) in ethanol (45 mL) and THF (45 mL) was added 10% Pd/C (100 mg). The solution was hydrogenated under 1 atmosphere of hydrogen for 16 hours at ambient temperature. The mixture was filtered through a plug of Celite and the volatiles were evaporated in vacuo. The resulting solid was triturated with 1:1 CH2Cl2-hexanes and air-dried to provide the title compound (1.31 g, 8.29 mmol, 94% yield) as a light green solid. 1H NMR (300 MHz, DMSO-d6) δ 9.00 (s, 1H), 7.78 (d, J=0.6 Hz, 1H), 7.25 (d, J=7.5 Hz, 1H), 7.18 (d, J=8.0 Hz, 1H), 6.80 (dd, J=7.4, 1.2 Hz, 1H), 5.84 (s, 2H), 2.58 (s, 3H); MS (ESI) m/z 159 (M+H)+.

Workup

  1. filtrationThe mixture was filtered through a plug of Celite
  2. customthe volatiles were evaporated in vacuo
  3. customThe resulting solid was triturated with 1:1 CH2Cl2-hexanes
  4. customair-dried

Sources & evidence

ORD record
ord-938e0a16484e43f6922b772be2eb5799
Source dataset
uspto-grants-2013_12
Patent number
US08604053B2

Reaction notes

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