2,3-Dichloro-5,6-dicyano-1,4-benzoquinone → HCID 10138371, compound

HRID 1826986Notes

Reaction equation

HRID 1826986 reaction equation
[NH:1]=[C:2]1[C:11]([C:12]#[N:13])=[C:10]([C:14]2[CH:19]=[C:18]([O:20][CH3:21])[C:17]([O:22][CH3:23])=[C:16]([Br:24])[CH:15]=2)[C:9]2[C:4](=[CH:5][C:6]([N:25]([CH3:27])[CH3:26])=[CH:7][CH:8]=2)[O:3]1.N[C:29]1OC2C(C(C3C=C(OC)C(OC)=C(Br)C=3)C=1C#N)=CC=CC=2.ClC1C(=O)C(C#N)=C(C#N)C(=O)C=1Cl>ClCCl.C(OCC)(=O)C>[NH2:1][C:2]1[O:3][C:4]2[C:9]([C:10]([C:14]3[CH:19]=[C:18]([O:20][CH3:21])[C:17]([O:22][CH3:23])=[C:16]([Br:24])[CH:15]=3)([CH3:29])[C:11]=1[C:12]#[N:13])=[CH:8][CH:7]=[C:6]([N:25]([CH3:27])[CH3:26])[CH:5]=2

Participants

6

Reactant 3

HCID 67752,3-Dichloro-5,6-dicyano-1,4-benzoquinoneHCID 10180948HCID 10180948, compoundHCID 10200202HCID 10200202, compound

Product 1

HCID 10138371HCID 10138371, compoundYield 79%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

2-Imino-3-cyano-7-dimethylamino-4-(3-bromo-4,5-dimethoxyphenyl)-chromene: 4 Å Molecular sieves (20 mg) was added to 2-amino-3-cyano-4-(3-bromo-4,5-dimethoxyphenyl)-4H-chromene (20 mg, 0.05 mmol) in dichloromethane (1 mL). The solution was stirred for 15 min. Then 2,3-dichloro-5,6-dicyano-1,4-benzoquinone (10 mg, 0.05 mmol, 1 eq.) was added and stirred continuously at room temperature for 1 h. The reaction mixture was diluted with ethyl acetate (20 mL) and washed with sodium bicarbonate saturated solution (20 mL), brine (20 mL), dried over sodium sulfate and concentrated to yield 17 mg (79%) of the desired compound. 1H NMR (DMSO-d6): 8.33 (s, 1H), 7.28 (d, J=1.9 Hz, 1H), 7.21 (d, J=1.9 Hz, 1H), 6.87 (d, J=9.1 Hz, 1H), 6.56 (dd, J=2.5, 9.1 Hz, 1H), 6.40 (d, J=2.5 Hz, 1H), 3.84 (s, 3H), 3.82 (s, 3H), 3.03 (s, 6H).

Workup

  1. stirringstirred continuously at room temperature for 1 h
  2. washwashed with sodium bicarbonate saturated solution (20 mL), brine (20 mL)
  3. dry with materialdried over sodium sulfate
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-d7f435e826454019a5163bc5303dfd0a
Source dataset
uspto-grants-2006_05
Patent number
US07053117B2

Reaction notes

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