Methanol → (R)-2-(6-Chloro-5-nitro-1-oxoisoquinolin-2(1H)-yl)propanamide

HRID 1161254Notes

Reaction equation

[Cl:1][C:2]1[C:3]([N+:13]([O-:15])=[O:14])=[C:4]2[C:9](=[CH:10][CH:11]=1)[C:8](=[O:12])O[CH:6]=[CH:5]2.CO.C(N(CC)CC)C.Cl.[NH2:26][C@H:27]([CH3:31])[C:28]([NH2:30])=[O:29]>>[Cl:1][C:2]1[C:3]([N+:13]([O-:15])=[O:14])=[C:4]2[C:9](=[CH:10][CH:11]=1)[C:8](=[O:12])[N:26]([C@H:27]([CH3:31])[C:28]([NH2:30])=[O:29])[CH:6]=[CH:5]2

Participants

Reactant 4

HCID 887Methanol

HCID 8471Triethylamine

HCID 2775814(2R)-2-Aminopropanamide hydrochloride

HCID 595157256-Chloro-5-nitro-1H-isochromen-1-one

Product 1

HCID 59515858(R)-2-(6-Chloro-5-nitro-1-oxoisoquinolin-2(1H)-yl)propanamide

Conditions

Temperature: 55 °C

Procedure

A round bottom flask was charged with 6-chloro-5-nitro-1H-isochromen-1-one (950 mg, 0.0042 mol), methanol (30 mL, 0.7 mol), triethylamine (0.64 mL, 0.0046 mol) and (R)-2-aminopropanamide hydrochloride (0.58 g, 0.0046 mol) and the reaction heated to 55° C. overnight. The reaction went to 90% completion. The solvent was removed and the residue purified by flash chromatography (40 g silica gel, 0-10% MeOH/DCM) to obtain the pure product as a light yellow solid. MS m/z=296.4 (M+H).

Workup

customThe solvent was removed
customthe residue purified by flash chromatography (40 g silica gel, 0-10% MeOH/DCM)

Sources & evidence

ORD record: ord-36837f9d697c4b529416a29e9df5e147
Source dataset: uspto-grants-2010_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07816371B2

Reaction notes

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