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

HRID 1161199Notes

Reaction equation

HRID 1161199 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.Br.[NH2:25][C@@H:26]([CH3:30])[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]([CH3:30])[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 18632422L-Alaninamide--hydrogen bromide (1/1)

Product 1

HCID 59515862(S)-2-(5-Nitro-1-oxoisoquinolin-2(1H)-yl)propanamide

Conditions

Temperature
50 °C

Procedure

A round bottom flask was charged with 5-nitro-isochromen-1-one (1.5 g, 0.0078 mol), methanol (20 mL, 0.4 mol), triethylamine (2 mL, 0.02 mol) and (S)-2-aminopropanamide hydrobromide (1.6 g, 0.0094 mol) and the reaction was heated at 50° C. overnight. The reaction mixture was cooled to room temperature wherein the product precipitated out. The precipitate was filtered and dried to yield the pure product as a yellow solid. MS m/z=262.2 (M+H).

Workup

  1. temperatureThe reaction mixture was cooled to room temperature wherein the product
  2. customprecipitated out
  3. filtrationThe precipitate was filtered
  4. customdried

Sources & evidence

ORD record
ord-eb1b3c8683de43fabfbde7dd9cc94fd1
Source dataset
uspto-grants-2010_10
Patent number
US07816371B2

Reaction notes

Loading…