Resorcinol → HCID 3852173, compound

HRID 1826969Notes

Reaction equation

HRID 1826969 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:12]=[C:13]([Br:17])[C:14]=1[O:15][CH3:16])[CH:6]=[C:7]([C:10]#[N:11])[C:8]#[N:9].[C:18]1([CH:25]=[CH:24][CH:23]=[C:21]([OH:22])[CH:20]=1)[OH:19].N1CCCCC1>C(O)C>[NH2:9][C:8]1[O:19][C:18]2[C:25]([CH:6]([C:5]3[CH:4]=[C:3]([O:2][CH3:1])[C:14]([O:15][CH3:16])=[C:13]([Br:17])[CH:12]=3)[C:7]=1[C:10]#[N:11])=[CH:24][CH:23]=[C:21]([OH:22])[CH:20]=2

Participants

5

Reactant 3

HCID 5054ResorcinolHCID 8082PiperidineHCID 3773318HCID 3773318, compound

Product 1

HCID 3852173HCID 3852173, compoundYield 59.5%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a mixture of 3,4-dimethoxy-5-bromobenzylidenemalononitrile (293 mg, 1 mmol) and resorcinol (110 mg, 1 mmol) in ethanol (2 mL) was added piperidine (0.1 mL, 1 mmol). The mixture was refluxed for 2 h. The solvent was evaporated, the residue was purified by chromatography on silica gel with EtOAc and hexane (1:2) as eluant, yielding 240 mg (59.5%) of the title compound. 1H NMR (DMSO-d6): 9.77 (brs, 1H), 6.96–6.86 (m, 5H), 6.52 (d, J=8.1, 1H), 6.41 (s, 1H), 4.65 (s, 1H), 3.80 (s, 3H), 3.70 (s, 3H).

Workup

  1. temperatureThe mixture was refluxed for 2 h
  2. customThe solvent was evaporated
  3. customthe residue was purified by chromatography on silica gel with EtOAc and hexane (1:2) as eluant

Sources & evidence

ORD record
ord-bb454aabb72942a2882c3804532086d2
Source dataset
uspto-grants-2006_05
Patent number
US07053117B2

Reaction notes

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