Sulfuric Acid → HCID 20222395, compound

HRID 980301Notes

Reaction equation

HRID 980301 reaction equation
[O:1]=[C:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[C:4](=[O:11])[N:3]1[CH2:12][CH:13]([C:15]1[C:23]2[C:18](=[CH:19][CH:20]=[C:21]([C:24]#[N:25])[CH:22]=2)[NH:17][CH:16]=1)[CH3:14].S(=O)(=O)(O)O.[H][H]>[Pd].CO>[O:1]=[C:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[C:4](=[O:11])[N:3]1[CH2:12][CH:13]([C:15]1[C:23]2[C:18](=[CH:19][CH:20]=[C:21]([CH2:24][NH2:25])[CH:22]=2)[NH:17][CH:16]=1)[CH3:14]

Participants

6

Reactant 3

HCID 1118Sulfuric AcidHCID 12822515HCID 12822515, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 20222395HCID 20222395, compoundYield 232.9%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A suspension of 3-[2-[1,3-dihydro-1,3-dioxo-2H-isoindol-2-yl]1-methylethyl]-1H-indole-5-carbonitrile (1.4 g) and pre-reduced 10% palladium on charcoal (1.4 g) in methanol (100 ml) containing concentrated sulphuric acid (0.5 ml) was hydrogenated at room temperature and pressure until hydrogen uptake ceased. The catalyst was filtered off and the filtrate was evaporated to dryness to give a red oil (3.3 g) which was used without further purification.

Workup

  1. customwas hydrogenated at room temperature
  2. filtrationThe catalyst was filtered off
  3. customthe filtrate was evaporated to dryness

Sources & evidence

ORD record
ord-8862ea30966a4a98a10a34d8f12cd6c7
Source dataset
uspto-grants-1987_01
Patent number
US04636521

Reaction notes

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