Formamide → HCID 22648863, compound

HRID 393287Notes

Reaction equation

HRID 393287 reaction equation
Br[CH2:2][C:3]([C:5]1[CH:10]=[CH:9][C:8]([OH:11])=[C:7]([CH3:12])[CH:6]=1)=O.[CH:13]([NH2:15])=[O:14]>>[O:14]1[CH:2]=[C:3]([C:5]2[CH:10]=[CH:9][C:8]([OH:11])=[C:7]([CH3:12])[CH:6]=2)[N:15]=[CH:13]1

Participants

3

Reactant 2

HCID 713FormamideHCID 112184492-Bromo-1-(4-hydroxy-3-methylphenyl)ethanone

Product 1

HCID 22648863HCID 22648863, compoundYield 33%

Procedure

A solution of 2-bromo-1-(4-hydroxy-3-methylphenyl)ethanone (200 mg, 0.87 mmol) in formamide (10 mL) was heated to 110° C. for 24 h. The excess formamide was removed by distillation under reduced pressure. The resulting residue was partitioned between a pH 7.0 buffer solution (10 mL) and EtOAc (50 mL). The organic layer was washed with water (10 mL) and brine (10 mL), dried (MgSO4), filtered and concentrated under reduced pressure. The residue was purified by flash chromatography (Hexane:EtOAc, 1:1) to yield the title compound (51 mg, 33% yield).

Workup

  1. customThe excess formamide was removed by distillation under reduced pressure
  2. customThe resulting residue was partitioned between a pH 7.0 buffer solution (10 mL) and EtOAc (50 mL)
  3. washThe organic layer was washed with water (10 mL) and brine (10 mL)
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified by flash chromatography (Hexane:EtOAc, 1:1)

Sources & evidence

ORD record
ord-f61df3abbbf64cc7a48e7f723b7b5a9d
Source dataset
uspto-grants-2004_10
Patent number
US06806265B2

Reaction notes

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