2,3-Dichloro-5,6-dicyano-1,4-benzoquinone → Methyl 8-cyano-2-naphthoate

HRID 376806Notes

Reaction equation

HRID 376806 reaction equation
[C:1]([C:3]1[C:12]2[CH:11]=[C:10]([C:13]([O:15][CH3:16])=[O:14])[CH:9]=[CH:8][C:7]=2[CH2:6][CH2:5][CH:4]=1)#[N:2].ClC1C(=O)C(C#N)=C(C#N)C(=O)C=1Cl>O1CCOCC1>[C:1]([C:3]1[CH:4]=[CH:5][CH:6]=[C:7]2[C:12]=1[CH:11]=[C:10]([C:13]([O:15][CH3:16])=[O:14])[CH:9]=[CH:8]2)#[N:2]

Participants

4

Reactant 2

HCID 67752,3-Dichloro-5,6-dicyano-1,4-benzoquinoneHCID 14756558Methyl 8-cyano-5,6-dihydro-2-naphthoate

Product 1

HCID 14756562Methyl 8-cyano-2-naphthoateYield 73%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

Part A--A solution of methyl 8-cyano-5,6-dihydro-2-naphthoate (1.0 g, 0.0047 mol) and 2,3-dichloro-5,6-dicyano-1,4-benzoquinone (1.07 g, 0.0047 mol) in dioxane (50 mL) was stirred at 120° C. over 16 hours. The reaction mixture was poured into ice water and extracted with ethyl acetate. The combined organic layers were dried over anhydrous magnesium sulfate and evaporated to dryness under reduced pressure. The residue was purified by flash chromatography using ethyl acetate to give methyl 8-cyano-2-naphthoate (0.72 g, 0.0034 mol, 73%) as a tan solid. mp=178-182° C.; 1H NMR (CDCl3) d 8.95 (s, 1H), 8.3-8.2 (m, 1H), 8.15-8.10 (m, 1H), 8.0-7.95 (m, 2H), 7.7-7.6 (m, 1H), 4.05 (s, 1H).

Workup

  1. extractionextracted with ethyl acetate
  2. dry with materialThe combined organic layers were dried over anhydrous magnesium sulfate
  3. customevaporated to dryness under reduced pressure
  4. customThe residue was purified by flash chromatography

Sources & evidence

ORD record
ord-22c8f691137340bb97dac508fe5bea8b
Source dataset
uspto-grants-2000_02
Patent number
US06022523

Reaction notes

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