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

HRID 1173071Notes

Reaction equation

HRID 1173071 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-07f74522d2fa4fe9beae78210eecde07
Source dataset
uspto-grants-2010_11
Patent number
US07834050B2

Reaction notes

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