5-Nitro-2-pyrrolidin-1-ylmethylbenzoxazole → 2-[(Pyrrolidin-1-yl)methyl]-1,3-benzoxazol-5-amine

HRID 2400363Notes

Reaction equation

HRID 2400363 reaction equation
[N+:1]([C:4]1[CH:5]=[CH:6][C:7]2[O:11][C:10]([CH2:12][N:13]3[CH2:17][CH2:16][CH2:15][CH2:14]3)=[N:9][C:8]=2[CH:18]=1)([O-])=O>[Pd].CCOC(C)=O.CO>[NH2:1][C:4]1[CH:5]=[CH:6][C:7]2[O:11][C:10]([CH2:12][N:13]3[CH2:14][CH2:15][CH2:16][CH2:17]3)=[N:9][C:8]=2[CH:18]=1

Participants

4

Reactant 1

HCID 597669925-Nitro-2-pyrrolidin-1-ylmethylbenzoxazole

Product 1

HCID 597669972-[(Pyrrolidin-1-yl)methyl]-1,3-benzoxazol-5-amineYield 100%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 21584119Ethylacetate methanolSolvent

Procedure

To a solution of 5-nitro-2-[(pyrrolidin-1-yl)methyl]benzoxazole (300 mg, 1.21 mmol) in a mixed solvent of EtOAc-MeOH (1:1, 70 mL) was added 10% Pd—C (40 mg), the flask was purged with argon, then the argon was replaced with H2, the reaction mixture was stirred under H2 atmosphere for 30 min. After filtration through Celite, washed with ethyl acetate. The solvents were evaporated to provide 263 mg (100%) of 5-amino-2-[(pyrrolidin-1-yl)methyl]benzoxazole as a yellow solid.

Workup

  1. customthe flask was purged with argon
  2. filtrationAfter filtration through Celite
  3. washwashed with ethyl acetate
  4. customThe solvents were evaporated

Sources & evidence

ORD record
ord-0520fc1cf16541708cae4208b71cde02
Source dataset
uspto-grants-2014_08
Patent number
US08796259B2

Reaction notes

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