Formaldehyde → HCID 19424225, compound

HRID 128825Notes

Reaction equation

HRID 128825 reaction equation
N[C:2]1[C:7]([CH3:8])=[CH:6][CH:5]=[CH:4][N:3]=1.[NH:9]1[C:13]2[CH:14]=[CH:15][CH:16]=[CH:17][C:12]=2[N:11]=[N:10]1.[CH2:18]=O>CCO>[N:9]1([CH2:18][C:2]2[C:7]([CH3:8])=[CH:6][CH:5]=[CH:4][N:3]=2)[C:13]2[CH:14]=[CH:15][CH:16]=[CH:17][C:12]=2[N:11]=[N:10]1

Participants

5

Reactant 3

HCID 712FormaldehydeHCID 153472-Amino-3-methylpyridineHCID 178418385HCID 178418385, compound

Product 1

HCID 19424225HCID 19424225, compoundYield 33.4%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
20 °C

Procedure

A mixture of 2-amino-3-methylpyridine (43.28 g, 0.4 mol) and benzotriazole (47.65 g, 0.4 mol) in EtOH (500 mL) was treated over 5 minutes with formaldehyde (32.2 g of 37% solution, 0.4 mol). The mixture was stirred at 20° C. overnight, then cooled and filtered to give 2-[(1-benzotriazolyl)methyl]-3-methyl pyridine (30 g, 31%). A sample was crystallized from EtOH; mp 175°-177° C.

Workup

  1. temperaturecooled
  2. filtrationfiltered

Sources & evidence

ORD record
ord-1aaa672e8cf44501af3e7389bcc2b229
Source dataset
uspto-grants-1995_11
Patent number
US05464861

Reaction notes

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