2-[3-(Methyloxy)-4-nitrophenyl]-5-(1-pyrrolidinylmethyl)-1,3,4-oxadiazole → 2-(Methyloxy)-4-[5-(1-pyrrolidinylmethyl)-1,3,4-oxadiazol-2-yl]aniline

HRID 419340Notes

Reaction equation

HRID 419340 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:12]2[O:13][C:14]([CH2:17][N:18]3[CH2:22][CH2:21][CH2:20][CH2:19]3)=[N:15][N:16]=2)[CH:6]=[CH:7][C:8]=1[N+:9]([O-])=O>[Pt].CCOC(C)=O>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:12]2[O:13][C:14]([CH2:17][N:18]3[CH2:22][CH2:21][CH2:20][CH2:19]3)=[N:15][N:16]=2)[CH:6]=[CH:7][C:8]=1[NH2:9]

Participants

4

Reactant 1

HCID 594529402-[3-(Methyloxy)-4-nitrophenyl]-5-(1-pyrrolidinylmethyl)-1,3,4-oxadiazole

Product 1

HCID 594526182-(Methyloxy)-4-[5-(1-pyrrolidinylmethyl)-1,3,4-oxadiazol-2-yl]anilineYield 25.1%

Reagents, catalysts & solvents 2

HCID 23939PlatinumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 2-[3-(methyloxy)-4-nitrophenyl]-5-(1-pyrrolidinylmethyl)-1,3,4-oxadiazole (1.13 g, 3.70 mmol) and platinum on carbon (sulfided) in EtOAc (25 mL) was stirred under H2 (1 atm.) overnight. The mixture was filtered through Celite® and concentrated. Purification by flash chromatography provided the title compound of step B (0.26 g, 0.93 mmol, 25%). 1H NMR (400 MHz, DMSO-d6) δ ppm 1.62-1.71 (m, 4H), 2.48-2.57 (m, 4H), 3.76-3.85 (m, 5H), 5.51 (br. s., 2H), 6.64-6.71 (m, 1H), 7.25 (d, J=1.8 Hz, 1H), 7.29 (dt, J=8.1, 2.4 Hz, 1H).

Workup

  1. filtrationThe mixture was filtered through Celite®
  2. concentrationconcentrated
  3. customPurification by flash chromatography

Sources & evidence

ORD record
ord-84e3060610824a2ca916355020e794ad
Source dataset
uspto-grants-2012_01
Patent number
US08093239B2

Reaction notes

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