1,1-Dimethylhydrazine → HCID 21075743, compound

HRID 1373910Notes

Reaction equation

HRID 1373910 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.[CH3:22][N:23]([CH3:25])[NH2:24]>C(Cl)Cl.C([O-])([O-])=O.[Na+].[Na+].C(Cl)(Cl)Cl>[CH3:22][N:23]([CH3:25])[NH:24][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]

Participants

7

Reactant 3

HCID 59761,1-DimethylhydrazineHCID 8471TriethylamineHCID 112758084-Chloro-3-nitroquinoline

Product 1

HCID 21075743HCID 21075743, compoundYield 95.6%

Reagents, catalysts & solvents 3

HCID 6212ChloroformSolventHCID 6344DichloromethaneSolventHCID 10340Sodium CarbonateSolvent

Procedure

A solution of 4-chloro-3-nitroquinoline (5.00 g, 24.0 mmol) in 100 mL CH2Cl2 was cooled to 0° C. and treated with triethylamine (8.40 mL, 60.0 mmol) and N,N-dimethylhydrazine (5.65 mL, 74.4 mmol) under an atmosphere of nitrogen. After 18 h, the mixture was diluted with 2% Na2CO3 solution and CHCl3 and separated. The organic portion was washed with water and brine, dried over Na2SO4, filtered and concentrated under reduced pressure to yield 4-(2,2-dimethylhydrazino)-3-nitroquinoline (5.33 g) as a yellow/orange crystalline solid.

Workup

  1. customseparated
  2. washThe organic portion was washed with water and brine
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-a39002a68fa74f839fb462db935110ff
Source dataset
uspto-grants-2007_01
Patent number
US07163947B2

Reaction notes

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