Methanol → (R)-Methyl 2-(5-amino-1-oxoisoquinolin-2(1H)-yl)-3-methylbutanoate

HRID 1161259Notes

Reaction equation

HRID 1161259 reaction equation
[CH3:1][CH:2]([CH3:22])[C@@H:3]([N:8]1[CH:17]=[CH:16][C:15]2[C:10](=[CH:11][CH:12]=[CH:13][C:14]=2[N+:18]([O-])=O)[C:9]1=[O:21])[C:4]([O:6][CH3:7])=[O:5].CO>[Pd]>[NH2:18][C:14]1[CH:13]=[CH:12][CH:11]=[C:10]2[C:15]=1[CH:16]=[CH:17][N:8]([C@H:3]([CH:2]([CH3:22])[CH3:1])[C:4]([O:6][CH3:7])=[O:5])[C:9]2=[O:21]

Participants

4

Reactant 2

HCID 887MethanolHCID 59515729(R)-Methyl 3-methyl-2-(5-nitro-1-oxoisoquinolin-2(1H)-yl)butanoate

Product 1

HCID 59515897(R)-Methyl 2-(5-amino-1-oxoisoquinolin-2(1H)-yl)-3-methylbutanoate

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Procedure

(R)-methyl 3-methyl-2-(5-nitro-1-oxoisoquinolin-2(1H)-yl)butanoate (2.8 g, 0.0091 mol) was stirred with palladium 10% wt. on calcium carbonate (0.23 g, 0.00011 mol) in methanol (40 mL, 1 mol) under hydrogen (balloon) over 1 h at room temperature. The catalyst was filtered, the filtrate was concentrated to dryness and yielded a yellow oil. MS m/z 274.8 (M+H)+.

Workup

  1. filtrationThe catalyst was filtered
  2. concentrationthe filtrate was concentrated to dryness
  3. customyielded a yellow oil

Sources & evidence

ORD record
ord-2a0bbf4aa973420faf127f1497f0c772
Source dataset
uspto-grants-2010_10
Patent number
US07816371B2

Reaction notes

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