Methanol → (S)-2-(5-Amino-1-oxoisoquinolin-2(1H)-yl)-3-hydroxypropanamide

HRID 1161209Notes

Reaction equation

HRID 1161209 reaction equation
[OH:1][CH2:2][C@H:3]([N:7]1[CH:16]=[CH:15][C:14]2[C:9](=[CH:10][CH:11]=[CH:12][C:13]=2[N+:17]([O-])=O)[C:8]1=[O:20])[C:4]([NH2:6])=[O:5].CO>[Pd]>[NH2:17][C:13]1[CH:12]=[CH:11][CH:10]=[C:9]2[C:14]=1[CH:15]=[CH:16][N:7]([C@@H:3]([CH2:2][OH:1])[C:4]([NH2:6])=[O:5])[C:8]2=[O:20]

Participants

4

Reactant 2

HCID 887MethanolHCID 59515781HCID 59515781, compound

Product 1

HCID 59515818(S)-2-(5-Amino-1-oxoisoquinolin-2(1H)-yl)-3-hydroxypropanamide

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Procedure

A round bottom flask (250 mL) was charged with (S)-3-hydroxy-2-(5-nitro-1-oxoisoquinolin-2(1H)-yl)propanamide (0.2 g, 0.0007 mol) and methanol (20 mL, 0.5 mol) and palladium, 10% weight on charcoal (0.02 g, 0.0001 mol) was added and the flask was evacuated of air with the aid of vaccum and the reaction was stirred under an atmosphere of hydrogen (1 atm) with the aid of a balloon. The reaction was stirred for 45 minutes, in which time the reaction was complete. The reaction was filtered and the solvent removed under reduced pressure to yield the pure product as a light yellow solid. MS m/z=248.3 (M+H).

Workup

  1. additionwas added
  2. customthe flask was evacuated of air with the aid of vaccum
  3. stirringThe reaction was stirred for 45 minutes, in which time the reaction
  4. filtrationThe reaction was filtered
  5. customthe solvent removed under reduced pressure

Sources & evidence

ORD record
ord-6d528be8c6e3451aaf539c3840ff55a5
Source dataset
uspto-grants-2010_10
Patent number
US07816371B2

Reaction notes

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