2-Nitro-4-(quinolin-4-yloxy)-phenol → 2-Amino-4-(quinolin-4-yloxy)-phenol

HRID 491683Notes

Reaction equation

HRID 491683 reaction equation
[N+:1]([C:4]1[CH:9]=[C:8]([O:10][C:11]2[C:20]3[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=3)[N:14]=[CH:13][CH:12]=2)[CH:7]=[CH:6][C:5]=1[OH:21])([O-])=O>[Pd].CO>[NH2:1][C:4]1[CH:9]=[C:8]([O:10][C:11]2[C:20]3[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=3)[N:14]=[CH:13][CH:12]=2)[CH:7]=[CH:6][C:5]=1[OH:21]

Participants

4

Reactant 1

HCID 177550132-Nitro-4-(quinolin-4-yloxy)-phenol

Product 1

HCID 177558402-Amino-4-(quinolin-4-yloxy)-phenol

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

2-Nitro-4-(quinolin-4-yloxy)-phenol (prepared as described in Example 40, 3.1 g, 11 mmol, 1.0 eq.) was suspended into MeOH (100 mL) and the atmosphere was replaced by argon. The catalyst, 10% Pd/C, was added and the argon was replaced by a H2 atmosphere. The mixture was stirred for 16 h at balloon pressure at RT until TLC showed reaction done. The Pd/C was filtered, the MeOH removed and the crude was purified by column chromatography (10-100% EtOAc/Hexane to 2% MeOH/EtOAc) to yield 2-amino-4-(quinolin-4-yloxy)-phenol.

Workup

  1. customreaction
  2. filtrationThe Pd/C was filtered
  3. customthe MeOH removed
  4. customthe crude was purified by column chromatography (10-100% EtOAc/Hexane to 2% MeOH/EtOAc)

Sources & evidence

ORD record
ord-d664400073094aa1b565ee0913e1e56e
Source dataset
uspto-grants-2009_05
Patent number
US07531553B2

Reaction notes

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