Sodium Azide → 6-Azidomethyl-3-benzyloxy-2-methylpyridine

HRID 2417827Notes

Reaction equation

HRID 2417827 reaction equation
[CH2:1]([O:8][C:9]1[C:10]([CH3:17])=[N:11][C:12]([CH2:15]Cl)=[CH:13][CH:14]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[N-:18]=[N+:19]=[N-:20].[Na+]>C(O)C>[N:18]([CH2:15][C:12]1[N:11]=[C:10]([CH3:17])[C:9]([O:8][CH2:1][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)=[CH:14][CH:13]=1)=[N+:19]=[N-:20]

Participants

4

Reactant 2

HCID 33557Sodium AzideHCID 233218813-Benzyloxy-6-chloromethyl-2-methylpyridine

Product 1

HCID 233218626-Azidomethyl-3-benzyloxy-2-methylpyridine

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 3-benzyloxy-6-chloromethyl-2-methylpyridine (8.02 g) and sodium azide (5.98 g) in 400 ml of ethanol is heated at 80° for 4 hours. The reaction mixture is cooled, filtered and evaporated to yield a residue which is partitioned between ice-cold 0.5N NaOH (150 ml) and ether (150 ml). The organic phase is dried over sodium sulfate and evaporated to yield 6-azidomethyl-3-benzyloxy-2-methylpyridine, NMR: (CDCl3) 2.47 (3H), 4.27 (2H), 4.95 (2H). Lithium aluminum hydride (1.27 g) is added to a solution of 6-azidomethyl-3-benzyloxy-2-methylpyridine (7.18 g) in 120 ml of dry ether at room temperature. After stirring for 45 minutes, 1.3 ml of water, 1.3 ml of 15% sodium hydroxide and 3.8 ml of water are added sequentially. The salts are filtered off and the filtrate is evaporated to yield 6-aminomethyl-3-benzyloxy-2-methylpyridine; NMR: (CDCl3) 1.67 (2H), 2.47 (3H), 3.8 (2H), 4.95 (2H).

Workup

  1. temperatureThe reaction mixture is cooled
  2. filtrationfiltered
  3. customevaporated
  4. customto yield a residue which
  5. customis partitioned between ice-cold 0.5N NaOH (150 ml) and ether (150 ml)
  6. dry with materialThe organic phase is dried over sodium sulfate
  7. customevaporated

Sources & evidence

ORD record
ord-961d5afd08134f2b89bf2a4301bad796
Source dataset
uspto-grants-1984_09
Patent number
US04470986

Reaction notes

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