2,3-Dichloro-5,6-dicyano-1,4-benzoquinone → HCID 85336185, compound

HRID 1182455Notes

Reaction equation

HRID 1182455 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[NH:8][C:9](=[O:29])[CH:10]=[CH:11][C:12]([CH3:28])=[CH:13][CH:14]([CH3:27])[CH:15]([O:25]C)[C:16]1[CH:21]=[CH:20][C:19]([N:22]([CH3:24])[CH3:23])=[CH:18][CH:17]=1.ClC1C(=O)C(C#N)=C(C#N)C(=O)C=1Cl>C1C=CC=CC=1.C(OCC)(=O)C>[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[NH:8][C:9](=[O:29])[CH:10]=[CH:11][C:12]([CH3:28])=[CH:13][CH:14]([C:15](=[O:25])[C:16]1[CH:17]=[CH:18][C:19]([N:22]([CH3:24])[CH3:23])=[CH:20][CH:21]=1)[CH3:27]

Participants

5

Reactant 2

HCID 67752,3-Dichloro-5,6-dicyano-1,4-benzoquinoneHCID 72480340HCID 72480340, compound

Product 1

HCID 85336185HCID 85336185, compoundYield 7.4%

Reagents, catalysts & solvents 2

HCID 241BenzeneSolventHCID 8857Ethyl AcetateSolvent2×

Procedure

To a stirred solution of compound 34 (85 mg, 0.216 mmol) in wet benzene (2 mL, benzene: H2O=9:1) at room temperature was added 2,3-dichloro-5,6-dicyano-1,4-benzoquinone (DDQ, 98 mg, 0.432 mmol). After being stirred vigorously for 15 min., the mixture was diluted with ethyl acetate (30 mL), washed with water (2×5 mL), dried (anhydr.MgSO4), and concentrated. Purification by flash silica gel chromatography (50% ethyl acetate in hexanes, and then ethyl acetate only) afforded the title compound 35 (6 mg, 7% yield): 1H NMR (300 MHz, CDCl3) δ 7.83 (d, J=9.0, 2H), 7.87 (br. s, 1H), 7.29 (d, J=15.6 Hz, 1H), 7.27 (d, 7.8 Hz, 1H), 7.00 (m, 1H), 6.72 (m, 2H), 6.62 (d, J=9.0 Hz, 2H), 5.97 (d, J=15.6 Hz, 1H), 5.97 (d, J=9.3 Hz, 1H), 4.34 (dq, J=9.3, 6.9 Hz, 1H), 3.03 (s, 3H), 1.87 (br. s, 3H), 1.29 (d, J=6.9 Hz, 3H); 13C NMR (75 MHz, CDCl3) δ 12.6, 17.6, 39.9, 40.8, 110.7, 118.0, 119.0, 119.3, 123.8, 124.4, 125.1, 126.9, 130.6, 132.5, 140.8, 146.2, 153.4, 164.8, 198.6.

Workup

  1. washwashed with water (2×5 mL)
  2. dry with materialdried (anhydr.MgSO4)
  3. concentrationconcentrated
  4. customPurification by flash silica gel chromatography (50% ethyl acetate in hexanes

Sources & evidence

ORD record
ord-5cb37baa4e7340d99da1a88f9fcde94c
Source dataset
uspto-grants-2007_10
Patent number
US07288567B2

Reaction notes

Loading…