Hydrogen Bromide → HCID 178467222, compound

HRID 746093Notes

Reaction equation

HRID 746093 reaction equation
[C:1]([C:4]1[N:5]=[C:6]([CH2:9][C:10]2[CH:15]=[CH:14][C:13]([O:16]C)=[CH:12][CH:11]=2)[NH:7][CH:8]=1)(=[O:3])[CH3:2].Br>CC(O)=O>[C:1]([C:4]1[N:5]=[C:6]([CH2:9][C:10]2[CH:15]=[CH:14][C:13]([OH:16])=[CH:12][CH:11]=2)[NH:7][CH:8]=1)(=[O:3])[CH3:2]

Participants

4

Reactant 2

HCID 260Hydrogen BromideHCID 178489886HCID 178489886, compound

Product 1

HCID 178467222HCID 178467222, compoundYield 81%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A solution of XXVI (2.2 g, 0.01 mol), AcOH (10 mL) and 48% HBr (40 mL) was heated at reflux. After 24 hours, the solution was concentrated to dryness, neutralized with NaHCO3 to pH 8.5 and the mixture stirred at room temperature. The suspension was concentrated to dryness mixed with CH3OH (100 mL) and silica gel (20 g) and concentrated to dryness. The solid was placed on a silica gel column and the product eluted with 5% CH3OH--CHCl3 to yield 1.7 g (81%) of XXVII; m.p. 229°-31° C. (CH3CN).

Workup

  1. temperatureat reflux
  2. concentrationthe solution was concentrated to dryness
  3. concentrationThe suspension was concentrated to dryness
  4. additionmixed with CH3OH (100 mL) and silica gel (20 g)
  5. concentrationconcentrated to dryness
  6. washthe product eluted with 5% CH3OH

Sources & evidence

ORD record
ord-fd29e23631e8450480a049577d3b40e7
Source dataset
uspto-grants-1986_07
Patent number
US04602093

Reaction notes

Loading…