8-Nitroquinoline → 8-Nitroquinolin-7-amine

HRID 1615633Notes

Reaction equation

HRID 1615633 reaction equation
[N+:1]([C:4]1[CH:5]=[CH:6][CH:7]=[C:8]2[C:13]=1[N:12]=[CH:11][CH:10]=[CH:9]2)([O-:3])=[O:2].[I-].C[N+:16](C)(C)N.CC(C)([O-])C.[K+].[Cl-].[NH4+]>CS(C)=O>[N+:1]([C:4]1[C:5]([NH2:16])=[CH:6][CH:7]=[C:8]2[C:13]=1[N:12]=[CH:11][CH:10]=[CH:9]2)([O-:3])=[O:2]

Participants

6

Reactant 4

HCID 118308-NitroquinolineHCID 18683Hydrazinium, 1,1,1-trimethyl-, iodide (1:1)HCID 25517Ammonium ChlorideHCID 23665647Potassium tert-butoxide

Product 1

HCID 129549938-Nitroquinolin-7-amineYield 18%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

To a solution of 8-nitroquinoline (1.88 g, 10 mmol) and 1,1,1-trimethylhydrazinium iodide (3.03 g, 15 mmol) in anhydrous dimethyl sulfoxide (DMSO) (20 mL) was added potassium tert-butoxide (3.36 g, 30 mmol) as a solid. The mixture was stirred at room temperature for 1 h. The mixture was then poured into saturated aqueous ammonium chloride and extracted with EtOAc. The organic layers were concentrated and the residue was purified by silica gel column chromatography (eluting with PE/EtOAc v/v 2:1) to give 8-nitroquinolin-7-amine as a yellow solid (300 mg, yield 18%). ESI MS: m/z 189 [M+H]+. 1H NMR (400 MHz, CDCl3): δ 8.93 (dd, 1H, 3.2 Hz, 2J=1.6 Hz), 8.00 (dd, 1H, 1J=6.4 Hz, 2J=1.6 Hz), 7.69 (d, 1H, J=6.8 Hz), 7.29 (dd, 1H, 1J=6.0 Hz, 2J=3.2 Hz), 7.00 (d, 1H, J=7.2 Hz), 5.60 (s, 2H).

Workup

  1. extractionextracted with EtOAc
  2. concentrationThe organic layers were concentrated
  3. customthe residue was purified by silica gel column chromatography (
  4. washeluting with PE/EtOAc v/v 2:1)

Sources & evidence

ORD record
ord-88d6db43994f4182a9107cdef90ee653
Source dataset
uspto-grants-2014_07
Patent number
US08765760B2

Reaction notes

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