2-Amino-4-methylpyridine → HCID 20228670, compound

HRID 1731349Notes

Reaction equation

HRID 1731349 reaction equation
Br[CH:2]([CH3:15])[C:3]([C:5]1[CH:6]=[CH:7][C:8]2[O:12][C:11](=[O:13])[NH:10][C:9]=2[CH:14]=1)=O.[NH2:16][C:17]1[CH:22]=[C:21]([CH3:23])[CH:20]=[CH:19][N:18]=1>C(#N)C>[CH3:15][C:2]1[N:18]2[CH:19]=[CH:20][C:21]([CH3:23])=[CH:22][C:17]2=[N:16][C:3]=1[C:5]1[CH:6]=[CH:7][C:8]2[O:12][C:11](=[O:13])[NH:10][C:9]=2[CH:14]=1

Participants

4

Reactant 2

HCID 15332-Amino-4-methylpyridineHCID 139361585-(2-Bromopropanoyl)-1,3-benzoxazol-2(3H)-one

Product 1

HCID 20228670HCID 20228670, compoundYield 25.1%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A solution of 5-(2-bromopropionyl)-2-benzoxazolinone (5.4 g) and 2-amino-4-picoline (6.5 g) in acetonitrile (100 ml) was refluxed for an hour. The reaction mixture was evaporated in vacuo and the residue was poured into a suspension of water and ethyl acetate with stirring. The resultant mixture was acidified to pH 0.8 with 10% hydrochloric acid and stirred for 20 minutes at ambient temperature. The resultant precipitate was collected by filtration. The product was suspended in a mixture of water and ethyl acetate and the resultant mixture was adjusted to pH 8.0 with 20% potassium carbonate. The precipitate was collected by filtration and washed with water and ethyl acetate. The precipitate was recrystallized from an aqueous tetrahydrofuran to afford 5-(3,7-dimethylimidazo[1,2-a]pyridin-2-yl)-2-benzoxazolinone (1.4 g). mp. 276°-280° C. (dec.).

Workup

  1. customThe reaction mixture was evaporated in vacuo
  2. additionthe residue was poured into a suspension of water and ethyl acetate
  3. stirringstirred for 20 minutes at ambient temperature
  4. filtrationThe resultant precipitate was collected by filtration
  5. additionThe product was suspended in a mixture of water and ethyl acetate
  6. filtrationThe precipitate was collected by filtration
  7. washwashed with water and ethyl acetate
  8. customThe precipitate was recrystallized from an aqueous tetrahydrofuran

Sources & evidence

ORD record
ord-f8dcdd4692de42d581653276ddf66b9e
Source dataset
uspto-grants-1986_11
Patent number
US04621084

Reaction notes

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