2-Amino-4-methylpyridine → 6-(3,7-dimethylimidazo[1,2-a]pyridin-2-yl)-2-methyl-3-oxo-3,4-dihydro-2H-1,4-benzoxazine

HRID 1731338Notes

Reaction equation

HRID 1731338 reaction equation
Br[CH:2]([CH3:17])[C:3]([C:5]1[CH:6]=[CH:7][C:8]2[O:13][CH:12]([CH3:14])[C:11](=[O:15])[NH:10][C:9]=2[CH:16]=1)=O.[NH2:18][C:19]1[CH:24]=[C:23]([CH3:25])[CH:22]=[CH:21][N:20]=1>C(#N)C>[CH3:17][C:2]1[N:20]2[CH:21]=[CH:22][C:23]([CH3:25])=[CH:24][C:19]2=[N:18][C:3]=1[C:5]1[CH:6]=[CH:7][C:8]2[O:13][CH:12]([CH3:14])[C:11](=[O:15])[NH:10][C:9]=2[CH:16]=1

Participants

4

Reactant 2

HCID 15332-Amino-4-methylpyridineHCID 202286766-(2-Bromopropanoyl)-2-methyl-2H-1,4-benzoxazin-3(4H)-one

Product 1

HCID 202286656-(3,7-dimethylimidazo[1,2-a]pyridin-2-yl)-2-methyl-3-oxo-3,4-dihydro-2H-1,4-benzoxazineYield 45.3%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A solution of 6-(2-bromopropionyl)-2-methyl-3-oxo-3,4-dihydro-2H-1,4-benzoxazine (1.5 g) and 2-amino-4-picoline (1.6 g) in acetonitrile (60 ml) was refluxed for 2.5 hours and the reaction mixture was evaporated under reduced pressure. A mixture of ethyl acetate and 5% hydrochloric acid was added to the residue and the resultant mixture was stirred at ambient temperature for 30 minutes. The precipitate was collected by filtration and suspended in water. The mixture was adjusted to pH 7.5 with 20% aqueous potassium carbonate. The resultant mixture was extracted with chloroform and the extract was washed with brine and dried over magnesium sulfate. The solvent was removed in vacuo to afford a crystalline residue, which was recrystallized from a mixture of ethyl acetate and tetrahydrofuran to give 6-(3,7-dimethylimidazo[1,2-a]pyridin-2-yl)-2-methyl-3-oxo-3,4-dihydro-2H-1,4-benzoxazine (0.7 g).

Workup

  1. customthe reaction mixture was evaporated under reduced pressure
  2. additionA mixture of ethyl acetate and 5% hydrochloric acid
  3. additionwas added to the residue
  4. filtrationThe precipitate was collected by filtration
  5. extractionThe resultant mixture was extracted with chloroform
  6. washthe extract was washed with brine
  7. dry with materialdried over magnesium sulfate
  8. customThe solvent was removed in vacuo
  9. customto afford a crystalline residue, which
  10. customwas recrystallized from a mixture of ethyl acetate and tetrahydrofuran

Sources & evidence

ORD record
ord-3cbc8c6064be40f5b780eacded30f601
Source dataset
uspto-grants-1986_11
Patent number
US04621084

Reaction notes

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