2-((2-Methylcyclopropyl)methoxy)-6-nitrobenzonitrile → 2-Amino-6-((2-methylcyclopropyl)methoxy)benzonitrile

HRID 471754Notes

Reaction equation

HRID 471754 reaction equation
[CH3:1][CH:2]1[CH2:4][CH:3]1[CH2:5][O:6][C:7]1[CH:14]=[CH:13][CH:12]=[C:11]([N+:15]([O-])=O)[C:8]=1[C:9]#[N:10]>CCOC(C)=O.CCO.[Pd]>[NH2:15][C:11]1[CH:12]=[CH:13][CH:14]=[C:7]([O:6][CH2:5][CH:3]2[CH2:4][CH:2]2[CH3:1])[C:8]=1[C:9]#[N:10]

Participants

4

Reactant 1

HCID 667465932-((2-Methylcyclopropyl)methoxy)-6-nitrobenzonitrile

Product 1

HCID 667469012-Amino-6-((2-methylcyclopropyl)methoxy)benzonitrileYield 79.1%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 21584252Ethanol ethylacetateSolvent

Procedure

A solution of 2-((2-methylcyclopropyl)methoxy)-6-nitrobenzonitrile (example 254c) (0.29 g, 1.25 mmol) in EtOAc/EtOH 1:1 (30 mL) was hydrogenated in an H-cube apparatus using 10% Pd/C as catalyst. The solution was evaporated to give 2-amino-6-((2-methylcyclopropyl)methoxy)benzonitrile (0.20 g, 79%) as a yellow oil. MS 203 (MH+).

Workup

  1. customThe solution was evaporated

Sources & evidence

ORD record
ord-71a20ec5210b46c4bf97fffc20bd3d35
Source dataset
uspto-grants-2014_01
Patent number
US08633186B2

Reaction notes

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