6-Nitro-2-(2-pyrrolidin-1-yl-vinyl)-benzooxazole → 2-(2-Pyrrolidin-1-yl-vinyl)-benzooxazol-6-ylamine

HRID 219648Notes

Reaction equation

HRID 219648 reaction equation
[N+:1]([C:4]1[CH:19]=[CH:18][C:7]2[N:8]=[C:9]([CH:11]=[CH:12][N:13]3[CH2:17][CH2:16][CH2:15][CH2:14]3)[O:10][C:6]=2[CH:5]=1)([O-])=O>C(O)C.[Pd]>[N:13]1([CH:12]=[CH:11][C:9]2[O:10][C:6]3[CH:5]=[C:4]([NH2:1])[CH:19]=[CH:18][C:7]=3[N:8]=2)[CH2:17][CH2:16][CH2:15][CH2:14]1

Participants

4

Reactant 1

HCID 866232146-Nitro-2-(2-pyrrolidin-1-yl-vinyl)-benzooxazole

Product 1

HCID 866232152-(2-Pyrrolidin-1-yl-vinyl)-benzooxazol-6-ylamine

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A solution of 6-nitro-2-(2-pyrrolidin-1-yl-vinyl)-benzooxazole (8.5 mmol) and palladium/carbon (10%) (0.85 mmol) in ethanol (100 mL) is hydrogenated with the pressure of 50 psi at room temperature for 18 hours. The mixture is filtered and the filtrate is concentrated in vacuo to afford 2-(2-pyrrolidin-1-yl-vinyl)-benzooxazol-6-ylamine as a solid. 1H NMR (300 MHz, CDCl3): δ 1.82 (m, 4H), 3.2 (broad, 4H), 3.65 (broad, 2H), 4.92 (d, H), 6.49 (d, H), 6.64 (d, H), 7.19 (d, H), 7.60 (d, H).

Workup

  1. filtrationThe mixture is filtered
  2. concentrationthe filtrate is concentrated in vacuo

Sources & evidence

ORD record
ord-a09f55b6a72847b88c8aeb02f4dad2bd
Source dataset
uspto-grants-2012_06
Patent number
US08202863B2

Reaction notes

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