2,3-Dichloro-5,6-dicyano-1,4-benzoquinone → HCID 15838104, compound

HRID 1421218Notes

Reaction equation

HRID 1421218 reaction equation
[F:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[N:7]([CH3:11])[C:6]1[C:12](=[O:28])[N:13]([CH2:21][C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)[CH2:14][CH:15]([C:16]([N:18]([CH3:20])[CH3:19])=[O:17])[C:5]2=1.ClC1C(=O)C(C#N)=C(C#N)C(=O)C=1Cl>ClCCl>[F:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[N:7]([CH3:11])[C:6]1[C:12](=[O:28])[N:13]([CH2:21][C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)[CH:14]=[C:15]([C:16]([N:18]([CH3:20])[CH3:19])=[O:17])[C:5]2=1

Participants

4

Reactant 2

HCID 67752,3-Dichloro-5,6-dicyano-1,4-benzoquinoneHCID 9951752HCID 9951752, compound

Product 1

HCID 15838104HCID 15838104, compoundYield 52%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 2 g (5 mmol) of (±)-6-fluoro-N,N,9-trimethyl-1-oxo-2-(phenylmethyl)-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indole-4-carboxamide and of 1.6 g (7 mmol) of 2,3-dichloro-5,6-dicyano-1,4-benzoquinone in 250 ml of dichloromethane is stirred for 1 h. The organic phase is washed and dried over sodium sulphate. The solvent is evaporated under reduced pressure and the residue is purified by chromatography on a column of silica gel, elution being carried out with a mixture of dichloromethane and ethyl acetate. The product is crystallized from diethyl ether. 1 g (2.6 mmol) of product is obtained.

Workup

  1. washThe organic phase is washed
  2. dry with materialdried over sodium sulphate
  3. customThe solvent is evaporated under reduced pressure
  4. customthe residue is purified by chromatography on a column of silica gel, elution
  5. additionbeing carried out with a mixture of dichloromethane and ethyl acetate
  6. customThe product is crystallized from diethyl ether

Sources & evidence

ORD record
ord-bf8851c1fa2047aeb5a085ef44013b46
Source dataset
uspto-grants-2000_06
Patent number
US06075021

Reaction notes

Loading…