2,3-Dichloro-5,6-dicyano-1,4-benzoquinone → HCID 16747666, compound

HRID 1514662Notes

Reaction equation

HRID 1514662 reaction equation
[OH:1][CH2:2][C:3]1[N:8]([CH3:9])[C:7]([C:10]2[C:18]3[C:13](=[C:14]([CH2:19][CH:20]=[C:21]([CH3:23])[CH3:22])[CH:15]=[CH:16][CH:17]=3)[NH:12][CH:11]=2)=[C:6]([O:24]CC2C=CC(OC)=CC=2)[C:5](=[O:34])[CH:4]=1.C(C1C(=O)C(Cl)=C(Cl)C(=O)C=1C#N)#N>ClCCl.O>[OH:24][C:6]1[C:5](=[O:34])[CH:4]=[C:3]([CH2:2][OH:1])[N:8]([CH3:9])[C:7]=1[C:10]1[C:18]2[C:13](=[C:14]([CH2:19][CH:20]=[C:21]([CH3:23])[CH3:22])[CH:15]=[CH:16][CH:17]=2)[NH:12][CH:11]=1

Participants

5

Reactant 2

HCID 67752,3-Dichloro-5,6-dicyano-1,4-benzoquinoneHCID 58985886HCID 58985886, compound

Product 1

HCID 16747666HCID 16747666, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

To a stirring solution of 213 (75 mg, 0.16 mmol) in dichloromethane (1.5 mL) and water (88 μL) was added DDQ (38 mg, 0.17 mmol) at 0° C. After the cold bath was removed, the mixture was stirred for 2 h. The DDQH2 was removed by filtration and washed with EtOAc. The solution was washed with water and brine. The organic layer was dried over Na2SO4 and the solvent removed under vacuum. After flash column chromatography, the desired product was obtained as a yellow solid (45 mg, 81%). Mp: 215° C. (dec). 1H NMR (CDCl3): δ 1.65 (3H, s), 1.74 (3H, s), 2.49 (3H, s), 3.71 (2H, d, J=6.6 Hz), 4.67 (2H, s), 5.29 (1H, m), 5.67 (1H, s), 7.3-7.4 (2H, m), 7.81 (1H, m), 8.31 (1H, m). 13C NMR (CDCl3): δ 28.4, 30.9, 33.3, 34.7, 61.7, 109.7, 119.2, 123.5, 123.7, 125.0, 126.4, 127.6, 129.2, 129.9, 130.6, 133.8, 134.5, 137.7, 149.6, 160.5, 176.2. IR (KBr): 3360, 3197, 2971, 2856, 1604, 1552, 1298, 984 cm−1. HRMS (EI): m/z Calcd. C20H22N2O3 for [M+]338.1630. found 338.1632.

Workup

  1. customAfter the cold bath was removed
  2. customThe DDQH2 was removed by filtration
  3. washwashed with EtOAc
  4. washThe solution was washed with water and brine
  5. dry with materialThe organic layer was dried over Na2SO4
  6. customthe solvent removed under vacuum

Sources & evidence

ORD record
ord-4846ba8d12634301b1b5625bcba3dd34
Source dataset
uspto-grants-2012_07
Patent number
US08222279B2

Reaction notes

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