Water → 6-Aminomethyl-3-benzyloxy-2-methylpyridine

HRID 2417828Notes

Reaction equation

HRID 2417828 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[N:7]([CH2:10][C:11]1[N:16]=[C:15]([CH3:17])[C:14]([O:18][CH2:19][C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)=[CH:13][CH:12]=1)=[N+]=[N-].O.[OH-].[Na+]>CCOCC>[NH2:7][CH2:10][C:11]1[N:16]=[C:15]([CH3:17])[C:14]([O:18][CH2:19][C:20]2[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=2)=[CH:13][CH:12]=1

Participants

6

Reactant 4

HCID 962Water2×HCID 14798Sodium HydroxideHCID 21226445Aluminium lithium hydrideHCID 233218626-Azidomethyl-3-benzyloxy-2-methylpyridine

Product 1

HCID 233218896-Aminomethyl-3-benzyloxy-2-methylpyridine

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

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. filtrationThe salts are filtered off
  2. customthe filtrate is evaporated

Sources & evidence

ORD record
ord-383123880f9d496eb6bfef8cc80e4871
Source dataset
uspto-grants-1984_09
Patent number
US04470986

Reaction notes

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