8-Nitro-7-quinolinecarboxaldehyde → 8-Aminoquinoline-7-carboxaldehyde

HRID 513684

Reaction equation

HRID 513684 reaction equation
[N+:1]([C:4]1[C:5]([CH:14]=[O:15])=[CH:6][CH:7]=[C:8]2[C:13]=1[N:12]=[CH:11][CH:10]=[CH:9]2)([O-])=O>Cl.CCO.CC(O)=O.O.[Fe]>[NH2:1][C:4]1[C:5]([CH:14]=[O:15])=[CH:6][CH:7]=[C:8]2[C:13]=1[N:12]=[CH:11][CH:10]=[CH:9]2

Participants

5

Reactant 1

HCID 117695548-Nitro-7-quinolinecarboxaldehyde

Product 1

HCID 110520988-Aminoquinoline-7-carboxaldehydeYield 770.4%

Reagents, catalysts & solvents 3

HCID 313Hydrochloric AcidCatalystHCID 23925IronCatalystHCID 86584229Acetic acid ethanol waterSolvent

Procedure

8-nitroquinoline-7-carbaldehyde 204 (100 mg, 0.49 mmol), iron powder (0.02 ml, 4.95 mmol) and conc. HCl (2 drops) was suspended in a mixture of EtOH/AcOH/water (2:2:1) and the mixture was heated under reflux for 15 min and then stirred at room temperature for 25 min. The mixture was filtered and the filtrate was concentrated in vacuo. The residue was diluted with EtOAc and washed with sat. NaHCO3 solution until the pH remained neutral. The organic phase was purified by column chromatography with heptane/EtOAc (80:20) as the eluent to yield the title compound (650 mg, 38%).

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 15 min
  3. filtrationThe mixture was filtered
  4. concentrationthe filtrate was concentrated in vacuo
  5. additionThe residue was diluted with EtOAc
  6. washwashed with sat. NaHCO3 solution until the pH
  7. customThe organic phase was purified by column chromatography with heptane/EtOAc (80:20) as the eluent

Sources & evidence

ORD record
ord-d0af7041a7fd4111bd6cf442e30d7aa7
Source dataset
uspto-grants-2015_08
Patent number
US09102688B2

Linked notes

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