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

HRID 280234Notes

Reaction equation

HRID 280234 reaction equation
[Al].[Li].[N:3]([CH2:6][C:7]1[N:12]=[C:11]([CH3:13])[C:10]([O:14][CH2:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)=[CH:9][CH:8]=1)=[N+]=[N-].O.[OH-].[Na+]>CCOCC>[NH2:3][CH2:6][C:7]1[N:12]=[C:11]([CH3:13])[C:10]([O:14][CH2:15][C:16]2[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=2)=[CH:9][CH:8]=1

Participants

6

Reactant 4

HCID 962Water2×HCID 14798Sodium HydroxideHCID 16211445Aluminum;lithiumHCID 233218626-Azidomethyl-3-benzyloxy-2-methylpyridine

Product 1

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

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

Lithium aluminum hyride (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-4b51ad092c3a4cdd9124407c6634aca4
Source dataset
uspto-grants-1986_05
Patent number
US04588732

Reaction notes

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