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

HRID 1161237Notes

Reaction equation

HRID 1161237 reaction equation
[N+:1]([C:4]1[CH:13]=[CH:12][CH:11]=[C:10]2[C:5]=1[CH:6]=[CH:7]O[C:9]2=[O:14])([O-:3])=[O:2].CO.C(N(CC)CC)C.Cl.[NH2:25][C@H:26]([C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1)[C:27]([NH2:29])=[O:28]>>[N+:1]([C:4]1[CH:13]=[CH:12][CH:11]=[C:10]2[C:5]=1[CH:6]=[CH:7][N:25]([C@H:26]([C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1)[C:27]([NH2:29])=[O:28])[C:9]2=[O:14])([O-:3])=[O:2]

Participants

5

Reactant 4

HCID 887MethanolHCID 8471TriethylamineHCID 100127605-nitro-1H-isochromen-1-oneHCID 16216957(R)-2-Amino-2-phenylacetamide hydrochloride

Product 1

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

Conditions

Temperature
50 °C

Procedure

A round bottom flask was charged with 5-nitro-isochromen-1-one (2 g, 0.01 mol), methanol (20 mL, 0.5 mol), triethylamine (3 mL, 0.02 mol) and (R)-2-amino-2-phenylacetamide hydrochloride (2.3 g, 0.012 mol) and the reaction heated at 50° C. for 3 hours. The starting material disappeared and the solvent was removed under reduced pressure and the residue purified by flash chromatography (40 g silica gel, 0-10% MeOH/DCM) to obtain the product as a brown solid. MS m/z=324.3 (M+H).

Workup

  1. customthe solvent was removed under reduced pressure
  2. customthe residue purified by flash chromatography (40 g silica gel, 0-10% MeOH/DCM)

Sources & evidence

ORD record
ord-ff7ce1f2cd414c7dbe81675e1a5035d4
Source dataset
uspto-grants-2010_10
Patent number
US07816371B2

Reaction notes

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