1,5-Naphthyridine-3-carbonitrile, 4-chloro-6-methyl- → 6-Methyl-[1,5]naphthyridine-3-carbonitrile

HRID 968725Notes

Reaction equation

HRID 968725 reaction equation
Cl[C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([CH3:12])[N:10]=2)[N:5]=[CH:4][C:3]=1[C:13]#[N:14]>[Zn].CC(O)=O>[CH3:12][C:9]1[N:10]=[C:11]2[C:6](=[CH:7][CH:8]=1)[N:5]=[CH:4][C:3]([C:13]#[N:14])=[CH:2]2

Participants

4

Reactant 1

HCID 587242971,5-Naphthyridine-3-carbonitrile, 4-chloro-6-methyl-2×

Product 1

HCID 587243266-Methyl-[1,5]naphthyridine-3-carbonitrileYield 72.4%

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 176Acetic AcidSolvent

Procedure

To a solution of 4-chloro-6-methyl-[1,5]naphthyridine-3-carbonitrile (200.0 mg, 0.98 mmol) (compound 5, see Example 1)in AcOH (20 mL) was added Zinc dust (156.1 mg, 2.40 mmol) and the reaction mixture was stirred at r.t. for 2 hrs. The reaction mixture was filtered through celite and the filtrate was then concentrated. The residue was dissolved in AcOEt and washed with water, Sat. Na2CO3, brine and dried to yield 6-methyl-[1,5]naphthyridine-3-carbonitrile as a light brown solid (120.0 mg, 71.3%). HR-MS-EI (+) m/e calcd for C10H7N3(M+) 169.0640. found 169.0639.

Workup

  1. filtrationThe reaction mixture was filtered through celite
  2. concentrationthe filtrate was then concentrated
  3. dissolutionThe residue was dissolved in AcOEt
  4. washwashed with water, Sat. Na2CO3, brine
  5. customdried

Sources & evidence

ORD record
ord-86f823dfea2e464ab7b448ec399a90b8
Source dataset
uspto-grants-2007_12
Patent number
US07304074B2

Reaction notes

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