8-Nitroquinoline → 8-Nitroquinolin-7-amine

HRID 1771999Notes

Reaction equation

HRID 1771999 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, 1J=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-3aa0c947a88b44b6b29775cc5a80ff4d
Source dataset
uspto-grants-2016_02
Patent number
US09249162B2

Reaction notes

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