N-methyl-N-phenyl-hydrazine → 8-Amino-7-quinolinol

HRID 513382Notes

Reaction equation

HRID 513382 reaction equation
[OH:1][C:2]1[CH:11]=[C:10]2[C:5]([CH:6]=[CH:7][CH:8]=[N:9]2)=[CH:4][CH:3]=1.C1([N:18](C)N)C=CC=CC=1>>[OH:1][C:2]1[C:11]([NH2:18])=[C:10]2[C:5]([CH:6]=[CH:7][CH:8]=[N:9]2)=[CH:4][CH:3]=1

Participants

3

Reactant 2

HCID 36299N-methyl-N-phenyl-hydrazineHCID 1354268667-Hydroxyquinoline

Product 1

HCID 1357028268-Amino-7-quinolinolYield 31%

Conditions

Temperature
130 °C

Procedure

7-Hydroxyquinoline (1.1 g, 7.5 mmol) and 1-phenyl-1-methylhydrazine (0.92 g, 7.5 mmol) were combined and heated at 130° C. under nitrogen for 16 h. After cooling the solvent was partially evaporated, the crude product was purified by column chromatography with heptane/EtOAc (1:1) as the eluent to give the title compound (370 mg, 31%).

Workup

  1. temperatureAfter cooling the solvent
  2. customwas partially evaporated
  3. customthe crude product was purified by column chromatography with heptane/EtOAc (1:1) as the eluent

Sources & evidence

ORD record
ord-4c8eb3cee3134350b2a91b3a812b7a7e
Source dataset
uspto-grants-2015_08
Patent number
US09102688B2

Reaction notes

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