Acetic Acid → HCID 12647522, compound

HRID 2098980Notes

Reaction equation

HRID 2098980 reaction equation
[CH3:1][O:2][C:3]1[CH:12]=[C:11]2[C:6]([CH2:7][CH2:8][CH2:9][C:10]2=O)=[CH:5][CH:4]=1.[C:14](#[N:18])[CH2:15][C:16]#[N:17].C1(C)C=CC=CC=1.C([O-])(=O)C.[NH4+].C(O)(=O)C>>[CH3:1][O:2][C:3]1[CH:12]=[C:11]2[C:6]([CH2:7][CH2:8][CH2:9][C:10]2=[C:15]([C:14]#[N:18])[C:16]#[N:17])=[CH:5][CH:4]=1

Participants

6

Reactant 5

HCID 176Acetic AcidHCID 1140TolueneHCID 8010MalononitrileHCID 812767-Methoxy-1,2,3,4-tetrahydronaphthalen-1-oneHCID 517165Ammonium Acetate

Product 1

HCID 12647522HCID 12647522, compoundYield 73.3%

Procedure

To a solution of 7-methoxy-3,4-dihydronaphthalen-1(2H)-one 46.1 (10.0 g, 56.7 mmol, Aldrich) and malononitrile (4.07 mL, 64.7 mmol) in toluene (40.0 mL, 378 mmol) was added ammonium acetate (0.938 mL, 13.1 mmol) and acetic acid (3.90 mL, 68.1 mmol). The mixture was refluxed vigorously for 17 hours and water was removed using a Dean Stark trap under the reflux condenser. The resulting mixture was concentrated and purified by silica gel column chromatography to give 48.1 (9.32 g, 73.2% yield). MS ESI (pos.) M/E: 225 (M+H).

Workup

  1. temperatureThe mixture was refluxed vigorously for 17 hours
  2. customwater was removed
  3. concentrationThe resulting mixture was concentrated
  4. custompurified by silica gel column chromatography

Sources & evidence

ORD record
ord-6129688a747648df822a1f0c02ec7540
Source dataset
uspto-grants-2013_05
Patent number
US08450522B2

Reaction notes

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