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

HRID 1161217Notes

Reaction equation

HRID 1161217 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][C@H:19]([CH3:23])[C:20]([NH2:22])=[O:21].C(N(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]([C@H:19]([CH3:23])[C:20]([NH2:22])=[O:21])[C:9]2=[O:14])([O-:3])=[O:2]

Participants

5

Reactant 4

HCID 887MethanolHCID 8471TriethylamineHCID 2775814(2R)-2-Aminopropanamide hydrochlorideHCID 100127605-nitro-1H-isochromen-1-one

Product 1

HCID 59515648(R)-2-(5-Nitro-1-oxoisoquinolin-2(1H)-yl)propanamide

Conditions

Temperature
52 °C

Procedure

To a solution of 5-nitro-isochromen-1-one (2 g, 0.01 mol) in methanol (40 mL, 1 mol) was added (R)-2-aminopropanamide hydrochloride (2.0 g, 0.016 mol) and triethylamine (2.6 mL, 0.019 mol) and stirred at 52° C. for 3 hr. The product (yellow solid) precipitated out and was filtered and carried on to the next reaction. MS m/z=262.1 (M+1).

Workup

  1. customThe product (yellow solid) precipitated out and
  2. filtrationwas filtered
  3. customcarried on to the next reaction

Sources & evidence

ORD record
ord-889dd0df1b734235a800b64cbfcf6a07
Source dataset
uspto-grants-2010_10
Patent number
US07816371B2

Reaction notes

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