4,5-Dichloro-3,6-dihydroxybenzene-1,2-dicarbonitrile → HCID 66915158, compound

HRID 880506Notes

Reaction equation

HRID 880506 reaction equation
Cl[C:2]1C(Cl)=C(O)C(C#N)=C(C#N)[C:3]=1O.[F:15][C:16]1[C:24]([N+:25]([O-:27])=[O:26])=[CH:23][CH:22]=[C:21]2[C:17]=1[CH2:18][CH2:19][NH:20]2>C1C=CC=CC=1>[CH2:2]([N:20]1[C:21]2[C:17](=[C:16]([F:15])[C:24]([N+:25]([O-:27])=[O:26])=[CH:23][CH:22]=2)[CH:18]=[CH:19]1)[CH3:3]

Participants

4

Reactant 2

HCID 2994934,5-Dichloro-3,6-dihydroxybenzene-1,2-dicarbonitrileHCID 669148564-fluoro-5-nitro-2,3-dihydro-1H-indole

Product 1

HCID 66915158HCID 66915158, compoundYield 72%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

2,3-Dichloro-5,6-dicyanohydroquinone (1.02 g, 4.50 mmol) was added to the solution of 4-fluoro-5-nitro-2,3-dihydro-indole (0.47 g, 2.25 mmol) in benzene (30 mL) and the mixture was refluxed for 7 h. The solvent was removed in vacuo and the residue partitioned between ethyl acetate (100 mL) and water (100 mL). The organic phase was washed with water (3×10 mL), brine (3×10 mL), dried over anhydrous sodium sulphate and concentration in vacuo afforded the crude product. Purification by column chromatography over neutral alumina using 5% ethyl acetate in hexane as eluent afforded 1-ethyl-4-fluoro-5-nitro-indole (0.33 g, 72%) as yellow solid.

Workup

  1. temperaturethe mixture was refluxed for 7 h
  2. customThe solvent was removed in vacuo
  3. customthe residue partitioned between ethyl acetate (100 mL) and water (100 mL)
  4. washThe organic phase was washed with water (3×10 mL), brine (3×10 mL)
  5. dry with materialdried over anhydrous sodium sulphate and concentration in vacuo
  6. customafforded the crude product
  7. customPurification by column chromatography over neutral alumina using 5% ethyl acetate in hexane as eluent

Sources & evidence

ORD record
ord-09dad58d72984935bd3d73107303cca8
Source dataset
uspto-grants-2015_03
Patent number
US08993574B2

Reaction notes

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