2-(Imidazo(1,2-a)pyridin-2-yl)ethan-1-amine → 2-(2-Formamidoethyl)imidazo [1,2-a]pyridine

HRID 918338Notes

Reaction equation

HRID 918338 reaction equation
[NH2:1][CH2:2][CH2:3][C:4]1[N:5]=[C:6]2[CH:11]=[CH:10][CH:9]=[CH:8][N:7]2[CH:12]=1.[O:13]=[CH:14]C(Cl)(Cl)Cl.C(Cl)(Cl)Cl>>[CH:14]([NH:1][CH2:2][CH2:3][C:4]1[N:5]=[C:6]2[CH:11]=[CH:10][CH:9]=[CH:8][N:7]2[CH:12]=1)=[O:13]

Participants

3

Reactant 2

HCID 75365162-(Imidazo(1,2-a)pyridin-2-yl)ethan-1-amineHCID 86733719Chloroform chloral

Product 1

HCID 542888482-(2-Formamidoethyl)imidazo [1,2-a]pyridine

Procedure

To a stirred solution of 2-(2-aminoethyl)imidazo [1,2-a] pyridine in chloroform chloral was added dropwise and stirring continued at room temperature for an hour. A solid precipitate was filtered off and recrystallised to give 2-(2-formamidoethyl)imidazo [1,2-a]pyridine. The 2-(2-formamidoethyl)imidazo [1,2-a]pyridine was gradually added to a slurry of lithium aluminium hydride in anhydrous tetrahydrofuran and the resultant suspension heated under reflux for 3 hours. By extracting the reaction mixture with dilute hydrochloric acid there was isolated 2-(2-methylaminoethyl)imidazo [1,2-a]pyridine dihydrochloride.

Workup

  1. waitcontinued at room temperature for an hour
  2. filtrationA solid precipitate was filtered off
  3. customrecrystallised

Sources & evidence

ORD record
ord-ec3966fdd90342618a522a01af3668a6
Source dataset
uspto-grants-1976_07
Patent number
US03970753

Reaction notes

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