HCID 21075743, compound → HCID 21075744, compound

HRID 1373911Notes

Reaction equation

HRID 1373911 reaction equation
[CH3:1][N:2]([CH3:17])[NH:3][C:4]1[C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[N:7]=[CH:6][C:5]=1[N+:14]([O-])=O>C(#N)C.[Pt]>[CH3:1][N:2]([CH3:17])[NH:3][C:4]1[C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[N:7]=[CH:6][C:5]=1[NH2:14]

Participants

4

Reactant 1

HCID 21075743HCID 21075743, compound

Product 1

HCID 21075744HCID 21075744, compoundYield 99.7%

Reagents, catalysts & solvents 2

HCID 23939PlatinumCatalystHCID 6342AcetonitrileSolvent

Procedure

A suspension of 4-(2,2-dimethylhydrazino)-3-nitroquinoline (5.33 g, 23.0 mmol) in 125 mL of acetonitrile was treated with 5% platinum on carbon (0.45 g, 0.11 mmol) and the mixture was shaken under an atmosphere of hydrogen (3.8×105 Pa). After 5 h, the reaction mixture was filtered through a pad of CELITE filter agent and rinsed with 80:20 acetonitrile:MeOH. The filtrate was concentrated under reduced pressure. The resulting oil was dissolved in CH2Cl2, dried over Na2SO4, filtered and concentrated under reduced pressure to give 4-(2,2-dimethylhydrazino)quinolin-3-amine (4.64 g) as a red foam.

Workup

  1. filtrationthe reaction mixture was filtered through a pad of CELITE
  2. filtrationfilter agent
  3. washrinsed with 80:20 acetonitrile
  4. concentrationThe filtrate was concentrated under reduced pressure
  5. dissolutionThe resulting oil was dissolved in CH2Cl2
  6. dry with materialdried over Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-158975e36b3644cc8f0e250d84496e9d
Source dataset
uspto-grants-2007_01
Patent number
US07163947B2

Reaction notes

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