Hydrogen Bromide → HCID 178422731, compound

HRID 2231667Notes

Reaction equation

HRID 2231667 reaction equation
[NH2:1][C:2]1[C:9]([CH3:10])=[CH:8][C:7]([C:11]2[CH:12]=[CH:13][C:14]([O:17]C)=[N:15][CH:16]=2)=[CH:6][C:3]=1[CH:4]=[O:5].Br>C(O)C>[NH2:1][C:2]1[C:9]([CH3:10])=[CH:8][C:7]([C:11]2[CH:12]=[CH:13][C:14]([OH:17])=[N:15][CH:16]=2)=[CH:6][C:3]=1[CH:4]=[O:5]

Participants

4

Reactant 2

HCID 260Hydrogen BromideHCID 21285536HCID 21285536, compound

Product 1

HCID 178422731HCID 178422731, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

2-Amino-5-(2-methoxypyrid-5-yl)-3-methylbenzaldehyde (0.92g) was added to a stirred solution of hydrobromic acid (3 cm3 of a 60% w/w aqueous solution) in absolute ethanol (100 cm3) under nitrogen and the mixture was heated under reflux for 2 hours. The cooled solution was evaporated in vacuo, and the residue partitioned between 10% sodium carbonate solution (30 cm3) and dichloromethane (50 cm3). The organic phase was dried (MgSO4) and evaporated in vacuo to give a solid residue which was chromatographed in silica (Merck "MK 60.9385" [Trade Mark]) eluting with dichloromethane:methanol, 10:1. Combination and evaporation of appropriate fractions followed by recrystallisation from ethyl acetate afforded the title compound, m.p. 231°-234° (0.26 g).

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 2 hours
  3. customThe cooled solution was evaporated in vacuo
  4. customthe residue partitioned between 10% sodium carbonate solution (30 cm3) and dichloromethane (50 cm3)
  5. dry with materialThe organic phase was dried (MgSO4)
  6. customevaporated in vacuo
  7. customto give a solid residue which
  8. customwas chromatographed in silica (Merck "MK 60.9385" [Trade Mark])
  9. washeluting with dichloromethane
  10. customCombination and evaporation of appropriate fractions
  11. customfollowed by recrystallisation from ethyl acetate

Sources & evidence

ORD record
ord-a28ab19312d048cc8366b70316a7579d
Source dataset
uspto-grants-1988_11
Patent number
US04783467

Reaction notes

Loading…