HCID 178488918, compound → HCID 178515896, compound

HRID 235946Notes

Reaction equation

HRID 235946 reaction equation
[Br:1][C:2]1[N:3]=[C:4]([C:10]2[CH:15]=[CH:14][C:13]([O:16]C)=[CH:12][CH:11]=2)[NH:5][C:6]=1C(O)=O>CC(O)=O.Br>[Br:1][C:2]1[N:3]=[C:4]([C:10]2[CH:11]=[CH:12][C:13]([OH:16])=[CH:14][CH:15]=2)[NH:5][CH:6]=1

Participants

4

Reactant 1

HCID 178488918HCID 178488918, compound

Product 1

HCID 178515896HCID 178515896, compoundYield 73.2%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 260Hydrogen BromideSolvent

Procedure

A suspension of 9 (2.5 g, 0.008 mol) in AcOH (10 ml) and 48% HBr (40 ml) was heated at reflux for 15 hours. The solution was concentrated to dryness and stirred overnight with saturated NaHCO3. The suspension was filtered, the solids chromatographed on silica gel and eluted with 5% CH3OH--CHCl3 to yield 1.4 g (65%) of 11. An analytical sample was prepared by crystallization from CH3CN, m.p. 210°-212° C.

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 15 hours
  3. concentrationThe solution was concentrated to dryness
  4. filtrationThe suspension was filtered
  5. customthe solids chromatographed on silica gel
  6. washeluted with 5% CH3OH

Sources & evidence

ORD record
ord-dfbb616477244dbabdc5e017bbad5297
Source dataset
uspto-grants-1987_02
Patent number
US04642311

Reaction notes

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