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

HRID 1161205Notes

Reaction equation

HRID 1161205 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.Cl.[NH2:18][CH2:19][C:20]([NH2:22])=[O:21].C([Al](CC)CC)C>>[N+:1]([C:4]1[CH:13]=[CH:12][CH:11]=[C:10]2[C:5]=1[CH:6]=[CH:7][N:18]([CH2:19][C:20]([NH2:22])=[O:21])[C:9]2=[O:14])([O-:3])=[O:2]

Participants

5

Reactant 4

HCID 887MethanolHCID 2723639Glycinamide hydrochlorideHCID 100127605-nitro-1H-isochromen-1-oneHCID 16682930Triethylaluminum

Product 1

HCID 595157382-(5-Nitro-1-oxoisoquinolin-2(1H)-yl)acetamide

Conditions

Temperature
85 °C

Procedure

A round bottom flask was charged with 5-nitro-isochromen-1-one (2.5 g, 0.013 mol), methanol (50 mL, 1 mol), glycinamide hydrochloride (3.0 g, 0.027 mol) and triethylaluminum (4.4 mL, 0.033 mol) and heated at 85° C. for 3 hours. The solvent was removed under reduced pressure to get the product as a yellow solid. MS m/z=248.2 (M+H).

Workup

  1. customThe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-eee6a1a50cba44d7bdd648036cc28789
Source dataset
uspto-grants-2010_10
Patent number
US07816371B2

Reaction notes

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