Methanol → (R)-2-(5-Amino-1-oxoisoquinolin-2(1H)-yl)-4-methylpentyl acetate

HRID 1161227Notes

Reaction equation

HRID 1161227 reaction equation
[C:1]([O:4][CH2:5][C@H:6]([N:11]1[CH:20]=[CH:19][C:18]2[C:13](=[CH:14][CH:15]=[CH:16][C:17]=2[N+:21]([O-])=O)[C:12]1=[O:24])[CH2:7][CH:8]([CH3:10])[CH3:9])(=[O:3])[CH3:2].CO>[Pd]>[C:1]([O:4][CH2:5][C@H:6]([N:11]1[CH:20]=[CH:19][C:18]2[C:13](=[CH:14][CH:15]=[CH:16][C:17]=2[NH2:21])[C:12]1=[O:24])[CH2:7][CH:8]([CH3:10])[CH3:9])(=[O:3])[CH3:2]

Participants

4

Reactant 2

HCID 887MethanolHCID 67087813(R)-4-Methyl-2-(5-nitro-1-oxoisoquinolin-2(1H)-yl)pentyl acetate

Product 1

HCID 67087974(R)-2-(5-Amino-1-oxoisoquinolin-2(1H)-yl)-4-methylpentyl acetate

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Procedure

Into a round bottom flask was combined (R)-4-methyl-2-(5-nitro-1-oxoisoquinolin-2(1H)-yl)pentyl acetate (3.00 g, 0.00903 mol), palladium on C (0.1 g, 0.0009 mol), and methanol (170 mL, 4.1 mol). The reaction mixture was stirred under hydrogen at room temperature and was monitored for progress. At 40 minutes, the reaction was completed by the absence of any starting material in the LC-MS analysis. The mixture was filtered twice using a DryDisk system to remove the catalyst. Volatiles were removed under vacuum and the mixture was purified by column chromatography using an ethyl acetate:hexanes (0-100%) gradient. The combined pure fractions were reduced in vacuo to yield the title compound as a yellow oil.

Workup

  1. customInto a round bottom flask was combined
  2. filtrationThe mixture was filtered twice
  3. customto remove the catalyst
  4. customVolatiles were removed under vacuum
  5. customthe mixture was purified by column chromatography

Sources & evidence

ORD record
ord-f6d7d8cb73134ae7b70353f61a335b80
Source dataset
uspto-grants-2010_10
Patent number
US07816371B2

Reaction notes

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