Ethanol → N~3~-Benzylpyridine-2,3-diamine

HRID 544450

Reaction equation

HRID 544450 reaction equation
[NH2:1][C:2]1[C:7]([NH2:8])=[CH:6][CH:5]=[CH:4][N:3]=1.C(O)C.[CH2:12](Br)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1>C(N(CC)CC)C>[NH2:1][C:2]1[C:7]([NH:8][CH2:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=[CH:6][CH:5]=[CH:4][N:3]=1

Participants

5

Reactant 3

HCID 702EthanolHCID 7498Benzyl BromideHCID 99562,3-Diaminopyridine

Product 1

HCID 10397869N~3~-Benzylpyridine-2,3-diamine

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Procedure

A mixture of 2,3-diaminopyridine (45 g), ethanol (500 ml), triethylamine (42 g) and benzyl bromide (70.5 g) was stirred at room temperature for 3 days. The solvent was evaporated in vacuo and the residue partitioned between chloroform (500 ml) and water (400 ml). The organic layer was eparated, filtered through a silica gel plug and evaporated in vacuo. The residue was triturated with hot chlorobutane to yield a brown powder.

Workup

  1. customThe solvent was evaporated in vacuo
  2. customthe residue partitioned between chloroform (500 ml) and water (400 ml)
  3. filtrationfiltered through a silica gel plug
  4. customevaporated in vacuo
  5. customThe residue was triturated with hot chlorobutane
  6. customto yield a brown powder

Sources & evidence

ORD record
ord-37275d50a019434292c0153254f8ffaa
Source dataset
uspto-grants-1984_05
Patent number
US04450164

Linked notes

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