Methanol → (R)-2-(5-Amino-1-oxoisoquinolin-2(1H)-yl)-2-phenylacetamide

HRID 1161235Notes

Reaction equation

HRID 1161235 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]([C@H:15]([C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)[C:16]([NH2:18])=[O:17])[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]([C@H:15]([C:19]1[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=1)[C:16]([NH2:18])=[O:17])[C:9]2=[O:14]

Participants

4

Reactant 2

HCID 887MethanolHCID 59515684(R)-2-(5-Nitro-1-oxoisoquinolin-2(1H)-yl)-2-phenylacetamide

Product 1

HCID 59515654(R)-2-(5-Amino-1-oxoisoquinolin-2(1H)-yl)-2-phenylacetamide

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Procedure

A round bottom flask was charged with (R)-2-(5-nitro-1-oxoisoquinolin-2(1H)-yl)-2-phenylacetamide (2.3 g, 0.0071 mol), methanol (30 mL, 0.7 mol) and palladium, 10% weight on charcoal (110 mg, 0.00090 mol) was added and the flask is evacuated of air and stirred under hydrogen atmosphere (1 atm) for 1.5 hours. The reaction mixture was filtered over celite and the solvent removed under pressure. The residue was purified by flash chromatography (40 g silica gel, 0-10% MeOH/DCM) to obtain the product as a light yellow solid. MS m/z=294.5(M+H).

Workup

  1. additionwas added
  2. customthe flask is evacuated of air
  3. filtrationThe reaction mixture was filtered over celite
  4. customthe solvent removed under pressure
  5. customThe residue was purified by flash chromatography (40 g silica gel, 0-10% MeOH/DCM)

Sources & evidence

ORD record
ord-8163db022c9141e488a2281e5d358445
Source dataset
uspto-grants-2010_10
Patent number
US07816371B2

Reaction notes

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