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

HRID 1161238Notes

Reaction equation

HRID 1161238 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>>[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

3

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

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) palladium, 10% weight on charcoal (110 mg, 0.00090 mol) was added and the flask was evacuated of air and stirred under hydrogen atmosphere (1 atm) for 1.5 h. The reaction mixture was filtered over celite and the solvent removed under pressure. The residue was purified by flash chromatography (40 g silica, 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 was 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, 0-10% MeOH/DCM)

Sources & evidence

ORD record
ord-d614033e64864752816352a61121f4ba
Source dataset
uspto-grants-2010_10
Patent number
US07816371B2

Reaction notes

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