2,3-Dichloro-5,6-dicyano-1,4-benzoquinone → HCID 59003387, compound

HRID 2199406Notes

Reaction equation

HRID 2199406 reaction equation
[CH3:1][CH:2]1[CH:10]([CH2:11][CH2:12][CH3:13])[C:9]2[C:4](=[CH:5][CH:6]=[C:7]([N+:14]([O-:16])=[O:15])[CH:8]=2)[N:3]1[CH2:17][C:18]([F:21])([F:20])[F:19].C(C1C(=O)C(Cl)=C(Cl)C(=O)C=1C#N)#N>CCOC(C)=O>[CH3:1][C:2]1[N:3]([CH2:17][C:18]([F:20])([F:19])[F:21])[C:4]2[C:9]([C:10]=1[CH2:11][CH2:12][CH3:13])=[CH:8][C:7]([N+:14]([O-:16])=[O:15])=[CH:6][CH:5]=2

Participants

4

Reactant 2

HCID 67752,3-Dichloro-5,6-dicyano-1,4-benzoquinoneHCID 69520098HCID 69520098, compound

Product 1

HCID 59003387HCID 59003387, compoundYield 60.4%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent3×

Procedure

In a 10 ml round bottom flask, equipped with a magnetic stirrer and under a dry nitrogen atmosphere, 20 mg of 2-methyl-5-nitro-3-propyl-1-(2,2,2-trifluoroethyl)-2,3-dihydro-1H-indole from last step was dissolved in EtOAc (3 mL), and 50 mg of DDQ was added to the solution and stirred at room temperature until TLC analysis (20% EtOAc in hexanes) showed no more starting material. The reaction mixture was diluted with ethyl acetate (10 mL) and washed with saturated sodium bicarbonate solution, water, and then brine and dried over MgSO4. The organic layer was absorbed on silica gel and purified by flash column chromatography, eluting with 10% EtOAc in hexanes. 12 mg of 2-methyl-5-nitro-3-propyl-1-(2,2,2-trifluoroethyl)-1H-indole was obtained. 1H NMR (500 MHz, CDCl3) δ 8.50 (d, J=2.0 Hz, 1H), 8.14 (dd, J=9.3, 2.0 Hz, 1H), 7.36 (d, J=9.3 Hz, 1H), 4.69 (q, J=8.5 Hz, 2H), 2.76 (t, J=7.6 Hz, 2H), 2.44 (s, 3H), 1.72-1.64 (m, 2H), 2.96 (t, J=7.3 Hz, 3H).

Workup

  1. customIn a 10 ml round bottom flask, equipped with a magnetic stirrer and under a dry nitrogen atmosphere
  2. washwashed with saturated sodium bicarbonate solution, water
  3. dry with materialbrine and dried over MgSO4
  4. customThe organic layer was absorbed on silica gel
  5. custompurified by flash column chromatography
  6. washeluting with 10% EtOAc in hexanes

Sources & evidence

ORD record
ord-baaa633b129642589c50726e9ab01ca8
Source dataset
uspto-grants-2016_06
Patent number
US09359285B2

Reaction notes

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