Methanol → HCID 19769405, compound

HRID 1590045Notes

Reaction equation

HRID 1590045 reaction equation
[CH3:1][N:2]1[CH2:7][CH2:6][CH:5]([N:8]2[C:17](=[O:18])[C:16]3[CH:19]=[CH:20][C:21]([N+:22]([O-])=O)=[C:14]4[C:15]=3[C:10](=[CH:11][CH:12]=[CH:13]4)[C:9]2=[O:25])[CH2:4][CH2:3]1.CO>O.[Pd]>[NH2:22][C:21]1[CH:20]=[CH:19][C:16]2[C:17](=[O:18])[N:8]([CH:5]3[CH2:4][CH2:3][N:2]([CH3:1])[CH2:7][CH2:6]3)[C:9](=[O:25])[C:10]3[C:15]=2[C:14]=1[CH:13]=[CH:12][CH:11]=3

Participants

5

Reactant 2

HCID 887MethanolHCID 9949784HCID 9949784, compound

Product 1

HCID 19769405HCID 19769405, compoundYield 79.6%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 962WaterSolvent

Procedure

A mixture of 2,3-dihydro-2-(1-methyl-piperidin-4-yl)-6-nitro-1H-benz[de]isoquinoline-1,3-dione (11.5 g; 33.9 mmol), prepared as in Example 3, in water (150 mL) and methanol (350 mL) was hydrogenated at atmospheric pressure over 10% Pd/C catalyst (1.4 g) for 5 hours. The catalyst was removed by filtration and the filtrate concentrated to a small volume. Isopropanol was added and the solution concentrated. Isopropanol was again added to the residue and the solution reconcentrated. The residue was swirled in ethanol and ether and the solid residue collected on a Buechner funnel. Drying under vacuum gave 6-amino-2,3-dihydro-2-(1-methylpiperidin-4-yl)-1H-benz[de]isoquinoline-1,3-dione (9.34 g; 27.0 mmol), m.p 345°-348° C.

Workup

  1. customThe catalyst was removed by filtration
  2. concentrationthe filtrate concentrated to a small volume
  3. additionIsopropanol was added
  4. concentrationthe solution concentrated
  5. additionIsopropanol was again added to the residue
  6. customether and the solid residue collected on a Buechner funnel
  7. customDrying under vacuum

Sources & evidence

ORD record
ord-28640b02a1cc4907ab870b1b3a6aa169
Source dataset
uspto-grants-1993_04
Patent number
US05202318

Reaction notes

Loading…