Hydrochloric Acid → HCID 178487723, compound

HRID 858019Notes

Reaction equation

HRID 858019 reaction equation
[CH3:1][O:2][C:3]1[CH:12]=[C:11]2[C:6]([C:7]([OH:16])=[C:8]([N+:13]([O-])=O)[CH:9]=[N:10]2)=[CH:5][CH:4]=1.[OH-].[NH4+].[ClH:19]>[Pd].CO.C(OCC)C>[ClH:19].[NH2:13][C:8]1[CH:9]=[N:10][C:11]2[C:6]([C:7]=1[OH:16])=[CH:5][CH:4]=[C:3]([O:2][CH3:1])[CH:12]=2

Participants

7

Reactant 3

HCID 313Hydrochloric AcidHCID 14923Ammonium HydroxideHCID 178487724HCID 178487724, compound

Product 1

HCID 178487723HCID 178487723, compound

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 887MethanolSolvent2×HCID 3283Diethyl EtherSolvent

Procedure

7-Methoxy-3-nitroquinolin-4-ol (4.5 g, 20.4 mmol), methanol (250 mL), ammonium hydroxide (5 mL) and palladium on carbon (400 mg of 10%) were combined. The mixture was placed on a Parr apparatus under a hydrogen atmosphere at 40 psi (2.8 Kg/cm2) for 2 hrs. The reaction mixture was filtered. The filtrate was concentrated under vacuum to provide a green solid. This material was dissolved in methanol (20 mL) and then 1N hydrochloric acid in diethyl ether (75 mL) was added. The resulting precipitate was isolated by filtration and dried to provide 2.6 g of 3-amino-7-methoxyquinolin-4-ol hydrochloride as a pink solid.

Workup

  1. filtrationThe reaction mixture was filtered
  2. concentrationThe filtrate was concentrated under vacuum
  3. customto provide a green solid
  4. customThe resulting precipitate was isolated by filtration
  5. customdried

Sources & evidence

ORD record
ord-12313c0eb734428da3837f4edd424a5e
Source dataset
uspto-grants-2006_12
Patent number
US07148232B2

Reaction notes

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