Methyl 2-cyano-4-nitrobenzoate → Methyl 4-amino-2-cyanobenzoate

HRID 2202379Notes

Reaction equation

HRID 2202379 reaction equation
[C:1]([C:3]1[CH:12]=[C:11]([N+:13]([O-])=O)[CH:10]=[CH:9][C:4]=1[C:5]([O:7][CH3:8])=[O:6])#[N:2]>CO.[Pd]>[NH2:13][C:11]1[CH:10]=[CH:9][C:4]([C:5]([O:7][CH3:8])=[O:6])=[C:3]([C:1]#[N:2])[CH:12]=1

Participants

4

Reactant 1

HCID 10104417Methyl 2-cyano-4-nitrobenzoate

Product 1

HCID 53419668Methyl 4-amino-2-cyanobenzoateYield 99.3%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a solution of methyl 2-cyano-4-nitrobenzoate (0.9 g, 4.4 mmol) in MeOH (5 mL) was added Pd/C (0.1 g). The resulting mixture was stirred at room temperature for 2 hours under hydrogen atmosphere. The mixture was filtered, and the filtrate was evaporated to dryness under reduced pressure to give the title product (0.77 g), which was used in the next step without further purification. LC-MS: m/z 177.2 (M+H)+

Workup

  1. filtrationThe mixture was filtered
  2. customthe filtrate was evaporated to dryness under reduced pressure

Sources & evidence

ORD record
ord-e4fc9c5326994cc29e02409e602dbea8
Source dataset
uspto-grants-2016_06
Patent number
US09365545B2

Reaction notes

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