Triethylamine → HCID 21075825, compound

HRID 1373956Notes

Reaction equation

HRID 1373956 reaction equation
[C:1]([O:5][C:6]([CH3:9])([CH3:8])[CH3:7])(=[O:4])[NH:2][NH2:3].C(N(CC)CC)C.[CH2:17]([O:24][C:25]1[CH:34]=[C:33]2[C:28]([C:29](Cl)=[C:30]([N+:35]([O-:37])=[O:36])[CH:31]=[N:32]2)=[CH:27][CH:26]=1)[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1>ClCCl.O.C(Cl)(Cl)Cl>[CH2:17]([O:24][C:25]1[CH:34]=[C:33]2[C:28]([C:29]([NH:3][NH:2][C:1]([O:5][C:6]([CH3:9])([CH3:8])[CH3:7])=[O:4])=[C:30]([N+:35]([O-:37])=[O:36])[CH:31]=[N:32]2)=[CH:27][CH:26]=1)[C:18]1[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=1

Participants

7

Reactant 3

HCID 8471TriethylamineHCID 70091tert-Butyl carbazateHCID 210757517-(Benzyloxy)-4-chloro-3-nitroquinoline

Product 1

HCID 21075825HCID 21075825, compoundYield 57.2%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6212ChloroformSolventHCID 6344DichloromethaneSolvent2×

Procedure

A solution of tert-butyl carbazate (33.1 g, 251 mmol) in 150 mL of dichloromethane was treated with triethylamine (66.5 mL, 502 mmol). The solution was placed under an atmosphere of nitrogen and cooled in a cold-water bath. The solution was treated with a solution of 7-benzyloxy-4-chloro-3-nitroquinoline (71.7 g, 228 mmol) in 350 mL of dichloromethane over 1 h. The reaction was stirred and allowed to warm to ambient temperature. After 15 h, the reaction was diluted with 200 mL of water and 250 mL of CHCl3 and the phases were separated. The organic portion was washed with water (200 mL), brine (200 mL), dried over Na2SO4, filtered and concentrated under reduced pressure to yield an orange solid. The solid was recrystallized from dichloromethane to yield 53.5 g of tert-butyl N′-(7-benzyloxy-3-nitroquinolin-4-yl)hydrazinecarboxylate as yellow crystals.

Workup

  1. temperaturecooled in a cold-water bath
  2. customthe phases were separated
  3. washThe organic portion was washed with water (200 mL), brine (200 mL)
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customto yield an orange solid
  8. customThe solid was recrystallized from dichloromethane

Sources & evidence

ORD record
ord-25088d4f06614f8e8d9c13425dbfe9c2
Source dataset
uspto-grants-2007_01
Patent number
US07163947B2

Reaction notes

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