Tetrahydrofuran → 1-Methylisoquinolin-5-amine

HRID 1911285Notes

Reaction equation

HRID 1911285 reaction equation
[CH3:1][C:2]1[C:11]2[C:6](=[C:7]([N+:12]([O-])=O)[CH:8]=[CH:9][CH:10]=2)[CH:5]=[CH:4][N:3]=1.O1CCCC1.[H][H]>CO.[Pd]>[CH3:1][C:2]1[C:11]2[CH:10]=[CH:9][CH:8]=[C:7]([NH2:12])[C:6]=2[CH:5]=[CH:4][N:3]=1

Participants

6

Reactant 3

HCID 8028TetrahydrofuranHCID 126479501-methyl-5-nitroIsoquinolineHCID 178418361HCID 178418361, compound

Product 1

HCID 99894901-Methylisoquinolin-5-amineYield 88%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

1-Methyl-5-nitroisoquinoline (prepared according to Rathelot, P. et al. Eur. J. Med. Chem. 1995, 30, 503-508.) (2.19 g, 11.64 mmol) was dissolved in methanol (20 mL) and tetrahydrofuran (20 mL) in a 250 mL stainless steel pressure bottle to which was added 5% Pd—C (0.438 g, 4.12 mmol). The reaction mixture was stirred for 2 h under 30 psi hydrogen at ambient temperature. The mixture was filtered through a nylon membrane and the volatiles evaporated in vacuo. The resulting grayish solid was triturated with 1:1 hexanes-CH2Cl2 (50 mL) and the title compound (1.62 g, 10.24 mmol, 88%) was collected as an off white solid. MS (DCI/NH3) m/z 159 (M+H)+.

Workup

  1. filtrationThe mixture was filtered through a nylon membrane
  2. customthe volatiles evaporated in vacuo
  3. customThe resulting grayish solid was triturated with 1:1 hexanes-CH2Cl2 (50 mL)

Sources & evidence

ORD record
ord-c5c03ef4b5bd4e14aab06ec82ac6492f
Source dataset
uspto-grants-2013_12
Patent number
US08604053B2

Reaction notes

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