Methanol → 5-Amino-2-(pyridin-2-ylmethyl)isoquinolin-1(2H)-one

HRID 1037781Notes

Reaction equation

HRID 1037781 reaction equation
[N+:1]([C:4]1[CH:13]=[CH:12][CH:11]=[C:10]2[C:5]=1[CH:6]=[CH:7][N:8]([CH2:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][N:17]=1)[C:9]2=[O:14])([O-])=O.CO>[Pd]>[NH2:1][C:4]1[CH:13]=[CH:12][CH:11]=[C:10]2[C:5]=1[CH:6]=[CH:7][N:8]([CH2:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][N:17]=1)[C:9]2=[O:14]

Participants

4

Reactant 2

HCID 887MethanolHCID 595795135-Nitro-2-(pyridin-2-ylmethyl)-1,2-dihydroisoquinolin-1-one

Product 1

HCID 595793535-Amino-2-(pyridin-2-ylmethyl)isoquinolin-1(2H)-one

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Procedure

Into a round bottom flask was combined 5-nitro-2-(pyridin-2-ylmethyl)isoquinolin-1(2H)-one (0.7 g, 0.002 mol), palladium/C (0.05 g, 0.0005 mol) and methanol (200 mL, 5 mol). The reaction mixture was stirred under hydrogen balloon at room temperature for 40 mins. The mixture was filtered over celite, MeOH was removed and the solid was yield (0.46 mg). MS m/z=252.4 (M+1). 1H NMR (DMSO) δ 8.49 (d, J=4.3 Hz, 1H), 7.74 (td, J=7.7, 1.6 Hz, 1H), 7.42 (t, J=7.3 Hz, 2H), 7.27 (dd, J=6.9, 5.0 Hz, 1H), 7.22-7.12 (m, 2H), 6.88 (d, J=7.2 Hz, 1H), 6.80 (d, J=7.6 Hz, 1H), 5.69 (s, 2H), 5.23 (s, 2H).

Workup

  1. customInto a round bottom flask was combined
  2. filtrationThe mixture was filtered over celite, MeOH
  3. customwas removed
  4. customthe solid was yield (0.46 mg)

Sources & evidence

ORD record
ord-5443ccd3db794be488bef2a79ed9e316
Source dataset
uspto-grants-2013_10
Patent number
US08546579B2

Reaction notes

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