Hexane → HCID 90102770, compound

HRID 1052630Notes

Reaction equation

HRID 1052630 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH:9]=[C:10]([OH:12])[CH:11]=1)[C:5]([NH:7][NH2:8])=[O:6].[N:13]#[C:14]Br.C(=O)(O)[O-].[Na+].CCCCCC>O1CCOCC1>[NH2:13][C:14]1[O:6][C:5]([C:4]2[CH:9]=[C:10]([OH:12])[CH:11]=[C:2]([Br:1])[CH:3]=2)=[N:7][N:8]=1

Participants

6

Reactant 4

HCID 8058HexaneHCID 10476Cyanogen BromideHCID 516892Sodium BicarbonateHCID 90102692HCID 90102692, compound

Product 1

HCID 90102770HCID 90102770, compoundYield 47.3%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

3-Bromo-5-hydroxybenzohydrazide (400 mg, 1.04 mmol) was suspended in 5 ml dioxane. Cyanogen bromide (110 mg, 1.04 mmol) and sodium bicarbonate (4%, 1 ml, 12 mmol) were added and the reaction was stirred at room temperature overnight. The reaction mixture was concentrated under reduced pressure and re-dissolved in ethyl acetate. The organic was washed with water, brine and dried over sodium sulphate, filtered and evaporated under reduced pressure. The oil obtained was precipitate with hexane and filtered to give 126 mg (43% yield) of the title compound. Purity 90%.

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. dissolutionre-dissolved in ethyl acetate
  3. washThe organic was washed with water, brine
  4. dry with materialdried over sodium sulphate
  5. filtrationfiltered
  6. customevaporated under reduced pressure
  7. customThe oil obtained
  8. filtrationfiltered

Sources & evidence

ORD record
ord-13c216359fae4b28a6673c4bd4ed7142
Source dataset
uspto-grants-2016_07
Patent number
US09388189B2

Reaction notes

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