Water → 6-(Pyrrolidin-1-yl)pyridin-3-amine

HRID 2364837Notes

Reaction equation

HRID 2364837 reaction equation
[N+:1]([C:4]1[CH:5]=[CH:6][C:7]([N:10]2[CH2:14][CH2:13][CH2:12][CH2:11]2)=[N:8][CH:9]=1)([O-])=O.CN(C=O)C.O>C1COCC1.[Ni]>[N:10]1([C:7]2[N:8]=[CH:9][C:4]([NH2:1])=[CH:5][CH:6]=2)[CH2:14][CH2:13][CH2:12][CH2:11]1

Participants

6

Reactant 3

HCID 962WaterHCID 6228DimethylformamideHCID 3168235-Nitro-2-(1-pyrrolidinyl)pyridine

Product 1

HCID 38991726-(Pyrrolidin-1-yl)pyridin-3-amineYield 97%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 8028TetrahydrofuranSolvent

Procedure

Material from Example 118A (9.52 g, 49.3 mmol) was dissolved in THF (50 mL) and DMF (40 mL) and added to a pressure bottle containing Raney Nickel 2800, water slurry (45%) (9.52 g, 162 mmol) stirred for 2 h at 30 psi under H2 gas. The solution was filtered through a nylon membrane, washed with CH3OH and the filtrate concentrated in vacuo to give the title compound (7.78 g, 97%). 1H NMR (400 MHz, DMSO-d6) δ ppm 1.81-1.91 (m, 4H) 3.17-3.29 (m, 4H) 4.30 (s, 2H) 6.25 (d, J=8.7, 1H), 6.90 (dd, J=2.8, 8.7, 1H), 7.55 (d, J=2.6, 1H). MS (ESI) m/z 164 (M+H)+.

Workup

  1. filtrationThe solution was filtered through a nylon membrane
  2. washwashed with CH3OH
  3. concentrationthe filtrate concentrated in vacuo

Sources & evidence

ORD record
ord-cb2f42459b03428db1f3f73d98caa9c2
Source dataset
uspto-grants-2014_04
Patent number
US08691938B2

Reaction notes

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