2-Nitro-5-(3-oxo-morpholin-4-yl)-benzonitrile → 2-Amino-5-(3-oxo-morpholin-4-YL)-benzonitrile

HRID 1819530Notes

Reaction equation

HRID 1819530 reaction equation
[N+:1]([C:4]1[CH:11]=[CH:10][C:9]([N:12]2[CH2:17][CH2:16][O:15][CH2:14][C:13]2=[O:18])=[CH:8][C:5]=1[C:6]#[N:7])([O-])=O>C1COCC1.[H][H].[Pd]>[NH2:1][C:4]1[CH:11]=[CH:10][C:9]([N:12]2[CH2:17][CH2:16][O:15][CH2:14][C:13]2=[O:18])=[CH:8][C:5]=1[C:6]#[N:7]

Participants

5

Reactant 1

HCID 588264662-Nitro-5-(3-oxo-morpholin-4-yl)-benzonitrile

Product 1

HCID 534164642-Amino-5-(3-oxo-morpholin-4-YL)-benzonitrileYield 60%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 8028TetrahydrofuranSolventHCID 178418361HCID 178418361, compoundSolvent

Procedure

2-Nitro-5-(3-oxo-morpholin-4-yl)-benzonitrile (1.1 g) was dissolved in THF (80 ml) and hydrogenated with hydrogen (1 atm) over Pd/C 10% (350 mg) for 18 h at 25° C. The reaction mixture was then filtered through decalite and precipitated (AcOEt/heptane) to yield 2-amino-5-(3-oxo-morpholin-4-yl)-benzonitrile as a white solid (580 mg). MH+=218.4

Workup

  1. filtrationThe reaction mixture was then filtered through decalite
  2. customprecipitated (AcOEt/heptane)

Sources & evidence

ORD record
ord-babec7680ff04e789b9bc3a12ed08238
Source dataset
uspto-grants-2009_10
Patent number
US07601752B2

Reaction notes

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