2,3-Dichloro-5,6-dicyano-1,4-benzoquinone → HCID 68725848, compound

HRID 2093620Notes

Reaction equation

HRID 2093620 reaction equation
[CH3:1][O:2][C:3]([C:5]1[CH:6]=[N:7][C:8]([CH:11]=[O:12])=[N:9][CH:10]=1)=[O:4].[NH2:13][C:14]1[CH:15]=[C:16]([CH:19]=[C:20]([CH:23]([CH3:25])[CH3:24])[C:21]=1O)[C:17]#[N:18].ClC1C(=O)C(C#N)=C(C#N)C(=O)C=1Cl>CO>[CH3:1][O:2][C:3]([C:5]1[CH:10]=[N:9][C:8]([C:11]2[O:12][C:21]3[C:20]([CH:23]([CH3:25])[CH3:24])=[CH:19][C:16]([C:17]#[N:18])=[CH:15][C:14]=3[N:13]=2)=[N:7][CH:6]=1)=[O:4]

Participants

5

Reactant 3

HCID 67752,3-Dichloro-5,6-dicyano-1,4-benzoquinoneHCID 57917216HCID 57917216, compoundHCID 77231520HCID 77231520, compound

Product 1

HCID 68725848HCID 68725848, compoundYield 35.8%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Methyl-2-formylpyrimidine-5-carboxylate (200 mg, 1.205 mmol) and 3-amino-4-hydroxy-5-isopropylbenzonitrile (212 mg, 1.205 mmol) were dissolved in methanol (5 ml). The mixture was concentrated, and then the residue was dissolved in dichloromethane (5 ml). To the above solution was added 2,3-dichloro-5,6-dicyano-p-benzoquinone (300.9 mg, 1.325 mmol) at room temperature. The solution was stirred at room temperature for 30 min, and then concentrated. The residue was partitioned between ethyl acetate and saturated aqueous sodium bicarbonate solution. The aqueous layer was extracted with ethyl acetate (3×). The combined organics were washed with brine, dried over magnesium sulfate, and concentrated. The residue was purified by flash chromatography (hexanes-ethyl acetate=4:1, then 1:1) to provide of the title compound (139 mg) as a yellow solid. Mass spectrum (ESI) 322.8 (M+1). 1H NMR (500 MHz, CDCl3) δ 9.55 (s, 2H), 8.13 (s, 1H), 7.66 (s, 1H), 4.09 (s, 3H), 3.65 (m, 1H), 1.50 (d, 6H, J=6.8 Hz).

Workup

  1. concentrationThe mixture was concentrated
  2. dissolutionthe residue was dissolved in dichloromethane (5 ml)
  3. concentrationconcentrated
  4. customThe residue was partitioned between ethyl acetate and saturated aqueous sodium bicarbonate solution
  5. extractionThe aqueous layer was extracted with ethyl acetate (3×)
  6. washThe combined organics were washed with brine
  7. dry with materialdried over magnesium sulfate
  8. concentrationconcentrated
  9. customThe residue was purified by flash chromatography (hexanes-ethyl acetate=4:1

Sources & evidence

ORD record
ord-91034a59220d4b45a7b366d8c1e8f212
Source dataset
uspto-grants-2013_05
Patent number
US08445480B2

Reaction notes

Loading…