Methanol → 4-Amino-2-hydroxybenzonitrile

HRID 1800486Notes

Reaction equation

HRID 1800486 reaction equation
[OH:1][C:2]1[CH:9]=[C:8]([N+:10]([O-])=O)[CH:7]=[CH:6][C:3]=1[C:4]#[N:5].CO>O1CCCC1.[C].[Pd]>[NH2:10][C:8]1[CH:7]=[CH:6][C:3]([C:4]#[N:5])=[C:2]([OH:1])[CH:9]=1

Participants

5

Reactant 2

HCID 887MethanolHCID 2861482-Hydroxy-4-nitrobenzonitrile

Product 1

HCID 124686824-Amino-2-hydroxybenzonitrileYield 97.1%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 2-hydroxy-4-nitrobenzonitrile (3.98 g, 24.25 mmol) in tetrahydrofuran (17 mL) were added methanol (70 mL) and 10% palladium-carbon (460 mg), and the mixture was stirred at room temperature for 14 hr under a hydrogen atmosphere (2.5 atm). The insoluble material was filtered off, and the filtrate was concentrated under reduced pressure to give the title compound (3.16 g, 97%) as a brown oil. This was used for the next reaction without further purification.

Workup

  1. filtrationThe insoluble material was filtered off
  2. concentrationthe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-742065b393cd4846ab33100168bcbd8f
Source dataset
uspto-grants-2013_01
Patent number
US08344135B2

Reaction notes

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