Methanol → 4,4-Dimethyl-1,3(2H,4H)-isoquinolinedione

HRID 1088934Notes

Reaction equation

HRID 1088934 reaction equation
N[C:2]1[CH:10]=[C:9]2[C:5]([C:6]([CH3:13])([CH3:12])[C:7](=[O:11])[NH:8]2)=[CH:4][C:3]=1[N+]([O-])=O.[CH3:17][OH:18]>[Pd]>[CH3:12][C:6]1([CH3:13])[C:5]2[C:9](=[CH:10][CH:2]=[CH:3][CH:4]=2)[C:17](=[O:18])[NH:8][C:7]1=[O:11]

Participants

4

Reactant 2

HCID 887MethanolHCID 13589235HCID 13589235, compound

Product 1

HCID 3380304,4-Dimethyl-1,3(2H,4H)-isoquinolinedione

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Procedure

A solution of 18.7 g. (0.085 mol) 6-amino-3,3-dimethyl-5-nitroindolin-2-one in 200 ml. methanol is hydrogenated at 40° C. in the presence of 1.9 g. of 10% Pd/C. The catalyst is filtered off with suction, the filtrate is evaporated and the residue is crystallised from ethanol. Yield: 15.6 g. (96% of theory); m.p. 245°-247° C.

Workup

  1. customis hydrogenated at 40° C. in the presence of 1.9 g
  2. filtrationThe catalyst is filtered off with suction
  3. customthe filtrate is evaporated
  4. customthe residue is crystallised from ethanol

Sources & evidence

ORD record
ord-b3c841b398e04645a68548cb7cad1d64
Source dataset
uspto-grants-1990_10
Patent number
US04963686

Reaction notes

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