Triethylamine → tert-butyl N'-(3-nitroquinolin-4-yl)hydrazinecarboxylate

HRID 1373882Notes

Reaction equation

HRID 1373882 reaction equation
Cl[C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[N:5]=[CH:4][C:3]=1[N+:12]([O-:14])=[O:13].C(N(CC)CC)C.[C:22]([O:26][C:27]([CH3:30])([CH3:29])[CH3:28])(=[O:25])[NH:23][NH2:24]>C(Cl)Cl>[N+:12]([C:3]1[CH:4]=[N:5][C:6]2[C:11]([C:2]=1[NH:24][NH:23][C:22]([O:26][C:27]([CH3:30])([CH3:29])[CH3:28])=[O:25])=[CH:10][CH:9]=[CH:8][CH:7]=2)([O-:14])=[O:13]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 70091tert-Butyl carbazate2×HCID 112758084-Chloro-3-nitroquinoline

Product 1

HCID 21075824tert-butyl N'-(3-nitroquinolin-4-yl)hydrazinecarboxylateYield 68.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 4-chloro-3-nitroquinoline (5.00 g, 24.0 mmol) in 120 mL of anhydrous CH2Cl2 was treated with triethylamine (6.7 mL, 48.2 mmol) and tert-butyl carbazate (3.20 g, 24.2 mmol). After stirring under nitrogen for 2.5 hour (h), an additional portion of tert-butyl carbazate (3.2 g, 24.2 mmol) was added. After stirring overnight, the deep red solution was washed with H2O (2×) and brine. The organic portion was dried over Na2SO4 and concentrated to give a red foam. The material was passed through a SiO2 column eluting with 2.5% methanol/CH2Cl2. The resulting red powder was treated with 5:1 hexanes/CH2Cl2 and filtered. The solid was washed several times with hexanes and was dried under vacuum to give tert-butyl N′-(3-nitroquinolin-4-yl)hydrazinecarboxylate (4.97 g) as an orange powder.

Workup

  1. stirringAfter stirring overnight
  2. washthe deep red solution was washed with H2O (2×) and brine
  3. dry with materialThe organic portion was dried over Na2SO4
  4. concentrationconcentrated
  5. customto give a red foam
  6. washeluting with 2.5% methanol/CH2Cl2
  7. additionThe resulting red powder was treated with 5:1 hexanes/CH2Cl2
  8. filtrationfiltered
  9. washThe solid was washed several times with hexanes
  10. customwas dried under vacuum

Sources & evidence

ORD record
ord-3ff7545468e3490abc908f510f4d8158
Source dataset
uspto-grants-2007_01
Patent number
US07163947B2

Reaction notes

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