Nitroxoline → 5-Amino-8-hydroxyquinoline

HRID 2259540Notes

Reaction equation

HRID 2259540 reaction equation
[OH:1][C:2]1[CH:3]=[CH:4][C:5]([N+:12]([O-])=O)=[C:6]2[C:11]=1[N:10]=[CH:9][CH:8]=[CH:7]2.[H][H]>[C].[Pd].C(O)(=O)C>[NH2:12][C:5]1[CH:4]=[CH:3][C:2]([OH:1])=[C:11]2[C:6]=1[CH:7]=[CH:8][CH:9]=[N:10]2

Participants

5

Reactant 2

HCID 19910Nitroxoline2×HCID 178418361HCID 178418361, compound3×

Product 1

HCID 4160025-Amino-8-hydroxyquinoline

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 176Acetic AcidSolvent

Procedure

5-Amino-8-hydroxyquinoline was prepared by the reduction of 8-hydroxy-5-nitroquinoline (from Aldrich Chemical Co., Inc., Milwaukee, Wis.). Twenty-five grams (0.131 moles) of 8-hydroxy-5-nitroquinoline were placed in a 500 milliliter (ml) Parr bottle followed by 250 ml of glacial acetic acid and 1 g of 10% palladium carbon. The bottle was further filled with 3×105Pascals (Pa) (3 atmospheres) of hydrogen. The filled bottle was attached to the Parr shaker-type hydrogenation apparatus (from Parr Instrument Co., Moline, Ill.) and the bottle and its contents were shaken until theoretical uptake was complete (approximately 5-6 hours). Reduction of the nitro group to the amine group was verified by the theoretical uptake of hydrogen. The original pressure in the Parr reactor was 0.61 MPa (88 psi). A drop of 0.24 MPa (34.7 psi) indicated that the theoretical uptake of hydrogen had occurred. The reaction contents were filtered, and the liquors were concentrated to a black-purple tar using a rotoevaporator. To remove excess acetic acid from the 5-amino-8-hydroxyquinoline, the tar was spread onto the bottom of an aluminum pan. The pan and its contents were heated in a vacuum oven for about 16 hours until the contents (5-amino-8-hydroxyquinoline) were dry.

Workup

  1. custom(approximately 5-6 hours)
  2. customThe reaction contents
  3. filtrationwere filtered
  4. concentrationthe liquors were concentrated to a black-purple tar
  5. customTo remove excess acetic acid from the 5-amino-8-hydroxyquinoline
  6. temperatureThe pan and its contents were heated in a vacuum oven for about 16 hours until the contents (5-amino-8-hydroxyquinoline)
  7. customwere dry

Sources & evidence

ORD record
ord-9a4dce2c0e954d1180b9450cad1d7eeb
Source dataset
uspto-grants-1995_12
Patent number
US05474827

Reaction notes

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