2,5-Dihydroxybenzoic acid → HCID 23448418, compound

HRID 1838780Notes

Reaction equation

HRID 1838780 reaction equation
[OH:1][C:2]1[CH:10]=[CH:9][C:8]([OH:11])=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].[N:12]12CCCN=C1C[CH2:16][CH2:15][CH2:14][CH2:13]2.BrCCCC#N.C(#N)C>O>[OH:1][C:2]1[CH:10]=[CH:9][C:8]([OH:11])=[CH:7][C:3]=1[C:4]([O:6][CH2:16][CH2:15][CH2:14][C:13]#[N:12])=[O:5]

Participants

6

Reactant 4

HCID 34692,5-Dihydroxybenzoic acidHCID 6342AcetonitrileHCID 214124-BromobutyronitrileHCID 811841,8-Diazabicyclo(5.4.0)undec-7-ene

Product 1

HCID 23448418HCID 23448418, compoundYield 78.4%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 2,5-dihydroxybenzoic acid (4.6 g; 30 mmol), 1,8-diazabicyclo[5.4.0]undec-7-ene (5.0 g; 33 mmol), 4-bromobutyronitrile (4.9 g; 33 mmol) and acetonitrile (70 ml) was heated under reflux overnight. The reaction mixture was added to water (500 ml) and extracted with ethyl acetate (3×100 ml). The combined organic layers were washed with 1N-hydrochloric acid (150 ml) and water (2×150 ml), dried over magnesium sulphate and filtered. The organic solvent was then removed in vacuo. The residue (6.2 g) was recrystallised from ethyl acetate/hexane to yield 5.2 g (78%) of the desired 3-cyanopropyl 2,5-dihydroxybenzoate.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux overnight
  3. extractionextracted with ethyl acetate (3×100 ml)
  4. washThe combined organic layers were washed with 1N-hydrochloric acid (150 ml) and water (2×150 ml)
  5. dry with materialdried over magnesium sulphate
  6. filtrationfiltered
  7. customThe organic solvent was then removed in vacuo
  8. customThe residue (6.2 g) was recrystallised from ethyl acetate/hexane

Sources & evidence

ORD record
ord-83cd8d3b9604423d84d1868a90317c53
Source dataset
uspto-grants-2004_01
Patent number
US06676851B1

Reaction notes

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