HCID 19093470, compound → HCID 19093455, compound

HRID 487063Notes

Reaction equation

HRID 487063 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([C:8]2[N:17]=[CH:16][CH:15]=[CH:14][C:9]=2[C:10]([O:12]C)=O)[CH:5]=[CH:6][CH:7]=1>[OH-].[Na+]>[Br:1][C:2]1[CH:3]=[C:4]2[C:5](=[CH:6][CH:7]=1)[C:10](=[O:12])[C:9]1[CH:14]=[CH:15][CH:16]=[N:17][C:8]2=1.[Br:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]2[C:3]=1[C:10](=[O:12])[C:9]1[CH:14]=[CH:15][CH:16]=[N:17][C:8]2=1

Participants

4

Reactant 1

HCID 19093470HCID 19093470, compound

Product 2

HCID 19093455HCID 19093455, compoundHCID 19093464HCID 19093464, compound

Reagents, catalysts & solvents 1

HCID 14798Sodium HydroxideSolvent

Procedure

A 500 mL r.b. flask containing 1 g of methyl 2-[3-bromophenyl]nicotinate and 30 g of polyphosphoric acid with a stirring bar was dipped in an oil bath at 210° C. While the contents were being warmed, house vacuum (~30 mmole) was slowly applied. After 15 mins., the reaction mixture started to stir easily and slowly started turning orange. This reaction mixture was stirred at 210° and 30 mm pressure for 4 hrs. The flask was taken out and while it was still warm, ~50 g of ice was cautiously added to the reaction mixture. After cooling the stirring reaction mixture to 0°, 60 mL of 5N sodium hydroxide was added slowly over 3 mins. The resulting green solid was filtered and washed thoroughly with 5×25 mL of water. This crude solid was taken up in methylene chloride and applied on silica gel and eluted with 1:20 ethyl acetate:hexane mixture to give a 1:2 ratio of 6-bromo-4-aza-9-fluorenone and 8-bromo-4-aza-9-fluorenone as yellow solids. ##STR18##

Workup

  1. customwas dipped in an oil bath at 210° C
  2. temperatureWhile the contents were being warmed
  3. stirringThis reaction mixture was stirred at 210°
  4. wait30 mm pressure for 4 hrs
  5. temperaturewas still warm
  6. temperatureAfter cooling
  7. customthe stirring reaction mixture to 0°
  8. filtrationThe resulting green solid was filtered
  9. washwashed thoroughly with 5×25 mL of water
  10. washeluted with 1:20 ethyl acetate

Sources & evidence

ORD record
ord-07a3675c809847b3a13de13bfbcdcbb0
Source dataset
uspto-grants-1994_03
Patent number
US05294610

Reaction notes

Loading…