Hydrazine → HCID 23008691, compound

HRID 1892254Notes

Reaction equation

HRID 1892254 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 (1×20 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 (1×20 mL)
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated
  5. washThe residue was washed with hexane

Sources & evidence

ORD record
ord-8441dca34b624447a61a71dbac9fdb5c
Source dataset
uspto-grants-2013_08
Patent number
US08507682B2

Reaction notes

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