Hydrazine → HCID 23008691, compound

HRID 2368679Notes

Reaction equation

HRID 2368679 reaction equation
Cl[C:2]1[CH:11]=[C:10]([CH3:12])[C:9]2[C:4](=[N:5][CH:6]=[CH:7][CH:8]=2)[N:3]=1.[NH2:13][NH2:14]>>[NH:13]([C:2]1[CH:11]=[C:10]([CH3:12])[C:9]2[C:4](=[N:5][CH:6]=[CH:7][CH:8]=2)[N:3]=1)[NH2:14]

Participants

3

Reactant 2

HCID 9321HydrazineHCID 17894863HCID 17894863, compound

Product 1

HCID 23008691HCID 23008691, compound

Procedure

A solution of 2-chloro-4-methyl-1,8-naphthyridine (330 mg, 1.8 mmol) in NH2NH2 was refluxed at 130° C. for 2 hours. The reaction mixture was cooled to room temperature, then excess NH2NH2 was removed on the rotary evaporator. The residue was taken up in 20 mL of CH2Cl2. The mixture was washed with saturated NaHCO3 (3×15 mL), brine (lx 20 mL), and then dried over MgSO4 and concentrated. The residue was washed with hexane to give 2-hydrazinyl-4-methyl-1,8-naphthyridine. Spectroscopic data: 1H NMR (300 MHz, CDCl3) δ ppm 2.56 (s, 3 H) 6.66 (s, 1 H) 7.22 (dd, J=7.91, 4.40 Hz, 1 H) 8.11 (dd, J=8.06, 1.90 Hz, 1 H) 8.82 (dd, 1 H).

Workup

  1. customexcess NH2NH2 was removed on the rotary evaporator
  2. washThe mixture was washed with saturated NaHCO3 (3×15 mL), brine (lx 20 mL)
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated
  5. washThe residue was washed with hexane

Sources & evidence

ORD record
ord-00898e4978044563883d0112f3d7d606
Source dataset
uspto-grants-2014_04
Patent number
US08703797B2

Reaction notes

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