2-(Hydroxyiminomethyl)quinolin-8-ol → 2-(Aminomethyl)quinolin-8-ol

HRID 623400

Reaction equation

HRID 623400 reaction equation
[OH:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:11]=1[N:10]=[C:9]([CH:12]=[N:13]O)[CH:8]=[CH:7]2>[Pd].[C].CO>[NH2:13][CH2:12][C:9]1[CH:8]=[CH:7][C:6]2[C:11](=[C:2]([OH:1])[CH:3]=[CH:4][CH:5]=2)[N:10]=1

Participants

4

Reactant 1

HCID 6047332-(Hydroxyiminomethyl)quinolin-8-ol

Product 1

HCID 5999672-(Aminomethyl)quinolin-8-olYield 82%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 887MethanolSolvent

Procedure

8-Hydroxy-quinoline-2-carboxaldehyde oxime D1 (167 mg, 0.888 mmol) and MeOH (50 mL) was treated under hydrogenolysis conditions (atmospheric H2, catalytic 10% Pd/carbon) at RT. After 4 h, the catalyst was filtered off and the volatiles removed which afforded 2-aminomethyl-quinolin-8-ol E1 as a light brown solid (126 mg, 82%); spectral data of this compound are given in Table 2.

Workup

  1. filtrationthe catalyst was filtered off
  2. customthe volatiles removed which

Sources & evidence

ORD record
ord-7056e7ae34984f5c9d181c58b9c74d53
Source dataset
uspto-grants-2016_04
Patent number
US09302993B2

Linked notes

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