Hydrochloric Acid → HCID 178487723, compound

HRID 1872653Notes

Reaction equation

HRID 1872653 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 1 N 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-b933a56df09a4086808c5ed0ddae032f
Source dataset
uspto-grants-2000_08
Patent number
US06110929

Reaction notes

Loading…