HCID 14391136, compound → HCID 21276193, compound

HRID 1381555Notes

Reaction equation

HRID 1381555 reaction equation
[CH3:1][N:2]1[C:10]2[C:5](=[CH:6][C:7]([N+:11]([O-])=O)=[CH:8][CH:9]=2)[C:4]([CH2:14][C:15]#[N:16])=[CH:3]1>C1COCC1.[Pd]>[CH3:1][N:2]1[C:10]2[C:5](=[CH:6][C:7]([NH2:11])=[CH:8][CH:9]=2)[C:4]([CH2:14][C:15]#[N:16])=[CH:3]1

Participants

4

Reactant 1

HCID 14391136HCID 14391136, compound

Product 1

HCID 21276193HCID 21276193, compoundYield 94.8%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 8.9 g (0.041 mole) of 1-methyl-5-nitroindole-3-acetonitrile in 600 ml of THF was added 3 g of 10% Pd/C. The mixture was hydrogenated in a Parr apparatus at 50 psi for 6 hours. The resulting mixture was filtered through celite treated with charcoal and filtered again through celite. The solvent was removed in vacuo leaving 7.2 g of the tan solid. This material was used directly without purification for the next step.

Workup

  1. filtrationThe resulting mixture was filtered through celite
  2. additiontreated with charcoal
  3. filtrationfiltered again through celite
  4. customThe solvent was removed in vacuo

Sources & evidence

ORD record
ord-067b08c155084aea8318914cdda2738a
Source dataset
uspto-grants-1989_02
Patent number
US04803218

Reaction notes

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