HCID 58099983, compound → HCID 58099976, compound

HRID 1465076Notes

Reaction equation

HRID 1465076 reaction equation
[CH:1]1([C:6]2[C:7]([OH:17])=[CH:8][C:9]([N+:14]([O-])=O)=[C:10]([CH:13]=2)[C:11]#[N:12])[CH2:5][CH2:4][CH2:3][CH2:2]1>C(O)C.[Pd]>[NH2:14][C:9]1[CH:8]=[C:7]([OH:17])[C:6]([CH:1]2[CH2:2][CH2:3][CH2:4][CH2:5]2)=[CH:13][C:10]=1[C:11]#[N:12]

Participants

4

Reactant 1

HCID 58099983HCID 58099983, compound

Product 1

HCID 58099976HCID 58099976, compoundYield 98.9%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A flask containing 10% Pd/C (4 mg) was evacuated and placed under a N2 atmosphere and suspended in ethanol (2 mL). To this was added 5-cyclopentyl-4-hydroxy-2-nitrobenzonitrile (42 mg, 0.18 mmol) as a solution in ethanol (1.5 mL). The reaction was stirred under H2 atmosphere for 2 h, then filtered and concentrated in vacuo to provide 2-amino-5-cyclopentyl-4-hydroxybenzonitrile as a yellow oil (36 mg, quantitative yield). LC/MS m/z 203.1 [M+H]+.

Workup

  1. customwas evacuated
  2. filtrationfiltered
  3. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-785175260da84b0f947a44cc22341bc2
Source dataset
uspto-grants-2015_04
Patent number
US08999976B2

Reaction notes

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