HCID 18926558, compound → HCID 18926522, compound

HRID 1600192Notes

Reaction equation

HRID 1600192 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]2[C:10](=[CH:11][CH:12]=1)[N:9]([CH2:13][CH2:14][C:15]([O:17][CH3:18])=[O:16])[CH:8]=[C:7]2[CH2:19][C:20]1[CH:21]=[N:22][CH:23]=[CH:24][CH:25]=1)([O-])=O>[Pd].CO>[NH2:1][C:4]1[CH:5]=[C:6]2[C:10](=[CH:11][CH:12]=1)[N:9]([CH2:13][CH2:14][C:15]([O:17][CH3:18])=[O:16])[CH:8]=[C:7]2[CH2:19][C:20]1[CH:21]=[N:22][CH:23]=[CH:24][CH:25]=1

Participants

4

Reactant 1

HCID 18926558HCID 18926558, compound

Product 1

HCID 18926522HCID 18926522, compoundYield 96%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A mixture of methyl 5-nitro-3-(3-pyridylmethyl)-1H-indole-1-propanoate (1.20 g) and 10% palladium on carbon (120 mg) in methanol (75 ml) was hydrogenated at 50° C. and 4.5 atm. until reduction was complete (2hours). The mixture was filtered and the catalyst was washed well with methanol. The filtrate and washings were combined and evaporated to give the title compound as an oil (1.05 g), Rf. 0.2(SS2). δ(CDCl3): 2.76(2H,t), 3.45(2H,br), 3.63(3H,s), 3.98(2H,s), 4.32(2H,t), 6.66-6.68(1H,dd), 6.72(1H,d), 6.77(1H,s), 7.11(1H,d), 7.14-7.18(1H,m), 7.48-7.51(1H,m), 8.42-8.44(1H,m), 8.56(1H,d).

Workup

  1. customwas hydrogenated at 50° C.
  2. custom(2hours)
  3. filtrationThe mixture was filtered
  4. washthe catalyst was washed well with methanol
  5. customevaporated

Sources & evidence

ORD record
ord-7f72e7c8362543a89f0e71cf2096c08e
Source dataset
uspto-grants-1998_04
Patent number
US05744488

Reaction notes

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