2,3-Dichloro-5,6-dicyano-1,4-benzoquinone → HCID 59375050, compound

HRID 1811146Notes

Reaction equation

HRID 1811146 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[CH:20]=[CH:19][C:18]([C:21]([NH2:23])=[O:22])=[C:17]2[C:9]=1[C:10]1[CH2:11][CH2:12][CH2:13][CH2:14][C:15]=1[NH:16]2.ClC1C(=O)C(C#N)=C(C#N)C(=O)C=1Cl>C1(C)C=CC=CC=1>[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[C:9]2[C:10]3[C:15](=[CH:14][CH:13]=[CH:12][CH:11]=3)[NH:16][C:17]=2[C:18]([C:21]([NH2:23])=[O:22])=[CH:19][CH:20]=1

Participants

4

Reactant 2

HCID 67752,3-Dichloro-5,6-dicyano-1,4-benzoquinoneHCID 59375058HCID 59375058, compound

Product 1

HCID 59375050HCID 59375050, compoundYield 19%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A solution of 5-(2-fluorophenyl)-2,3,4,9-tetrahydro-1H-carbazole-8-carboxamide (Example 47-1, 0.024 g, 0.078 mmol) in toluene (0.39 mL) was treated with 2,3-dichloro-5,6-dicyano-1,4-benzoquinone (0.039 g, 0.171 mmol), and the mixture was heated to reflux. After 4 h, the mixture was cooled to rt. The solid was removed by filtration and rinsed with EtOAc. The filtrate was concentrated, diluted with methanol and subjected to preparative HPLC. The product-containing effluent was treated with NaHCO3 (aq) and concentrated. The residue was extracted three times with DCM, and the combined organic layers were dried and concentrated to give 4-(2-fluorophenyl)-9H-carbazole-1-carboxamide (0.0045 g, 19%) as a light tan solid. Mass spectrum m/z 305.0 (M+H)+.

Workup

  1. temperaturethe mixture was heated to reflux
  2. customThe solid was removed by filtration
  3. washrinsed with EtOAc
  4. concentrationThe filtrate was concentrated
  5. additiondiluted with methanol
  6. additionThe product-containing effluent was treated with NaHCO3 (aq)
  7. concentrationconcentrated
  8. extractionThe residue was extracted three times with DCM
  9. customthe combined organic layers were dried
  10. concentrationconcentrated

Sources & evidence

ORD record
ord-f559207e100949afa37374bf1f4ce26d
Source dataset
uspto-grants-2013_01
Patent number
US08362065B2

Reaction notes

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