Ammonium Hydroxide → HCID 178422972, compound

HRID 1838830Notes

Reaction equation

HRID 1838830 reaction equation
[CH3:1][C:2]1[CH:11]=[C:10]2[C:5]([C:6]([OH:15])=[C:7]([N+:12]([O-])=O)[CH:8]=[N:9]2)=[CH:4][CH:3]=1.[OH-].[NH4+].[H][H]>[Pd].CO>[NH2:12][C:7]1[CH:8]=[N:9][C:10]2[C:5]([C:6]=1[OH:15])=[CH:4][CH:3]=[C:2]([CH3:1])[CH:11]=2

Participants

6

Reactant 3

HCID 14923Ammonium HydroxideHCID 178418361HCID 178418361, compoundHCID 178422973HCID 178422973, compound

Product 1

HCID 178422972HCID 178422972, compoundYield 84.1%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

7-Methyl-3-nitro-4-quinolinol (11.8 g, 58 mmol), methanol (about 300 mL), ammonium hydroxide (50 mL), and palladium on carbon (1 g of 10%) were combined. The mixture was placed on a Parr apparatus under a 35-40 psi (2.4-2.8 Kg/cm2) hydrogen atmosphere for about 1 hour. The reaction mixture was filtered through a layer of Celite® filter agent and the filter cake was rinsed well with methanol. The filtrate was treated with charcoal and then concentrated under vacuum to provide a fluffy pale green solid. This material was triturated with acetonitrile to provide 8.5 g of 3-amino-7-methyl-4-quinolinol.

Workup

  1. filtrationThe reaction mixture was filtered through a layer of Celite®
  2. filtrationfilter agent
  3. washthe filter cake was rinsed well with methanol
  4. additionThe filtrate was treated with charcoal
  5. concentrationconcentrated under vacuum
  6. customto provide a fluffy pale green solid
  7. customThis material was triturated with acetonitrile

Sources & evidence

ORD record
ord-a74520afc4ee4861a89913f407d7d419
Source dataset
uspto-grants-2004_01
Patent number
US06677334B2

Reaction notes

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