6,7-Dihydro-3-nitro-5H-cyclopenta[b]pyridine → 5H,6H,7H-cyclopenta[b]pyridin-3-amine

HRID 571978Notes

Reaction equation

HRID 571978 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]2[CH2:12][CH2:11][CH2:10][C:7]2=[N:8][CH:9]=1)([O-])=O>CO.[Pd]>[N:8]1[CH:9]=[C:4]([NH2:1])[CH:5]=[C:6]2[CH2:12][CH2:11][CH2:10][C:7]=12

Participants

4

Reactant 1

HCID 115645226,7-Dihydro-3-nitro-5H-cyclopenta[b]pyridine

Product 1

HCID 106305325H,6H,7H-cyclopenta[b]pyridin-3-amine

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

3-Nitro-6,7-dihydro-5H-cyclopenta[b]pyridine (C) (340 mg, 2.07 mmol) was dissolved in methanol. Pd/C (40 mg) was added to it. The resulting mixture was stirred at room temperature for 2 h under H2. TLC showed complete consumption of starting material. The mixture was filtered through celite bed and the filtrate was concentrated under reduced pressure to afford desired 6,7-dihydro-5H-cyclopenta[b]pyridin-3-amine (D). (250 mg, 90%)

Workup

  1. customconsumption of starting material
  2. filtrationThe mixture was filtered through celite bed
  3. concentrationthe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-c50034691c774b2d809c435f77861998
Source dataset
uspto-grants-2015_05
Patent number
US09029378B2

Reaction notes

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