2,3-Dichloro-5,6-dicyano-1,4-benzoquinone → HCID 68611887, compound

HRID 515382Notes

Reaction equation

HRID 515382 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]2[C:10](=[CH:11][CH:12]=1)[N:9]([CH:13]1[CH2:18][CH2:17][N:16]([C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])[CH2:15][CH2:14]1)[CH2:8][CH2:7]2)([O-:3])=[O:2].ClC1C(=O)C(C#N)=C(C#N)C(=O)C=1Cl.C(OCC)(=O)C>O1CCCC1>[N+:1]([C:4]1[CH:5]=[C:6]2[C:10](=[CH:11][CH:12]=1)[N:9]([CH:13]1[CH2:18][CH2:17][N:16]([C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])[CH2:15][CH2:14]1)[CH:8]=[CH:7]2)([O-:3])=[O:2]

Participants

5

Reactant 3

HCID 67752,3-Dichloro-5,6-dicyano-1,4-benzoquinoneHCID 8857Ethyl AcetateHCID 86671002HCID 86671002, compound

Product 1

HCID 68611887HCID 68611887, compoundYield 93%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

tert-Butyl 4-(5-nitroindolin-1-yl)piperidine-1-carboxylate (9.72 mmol, 3.377 g) was stirred at 0° C. in tetrahydrofuran (25 mL). 2,3-Dichloro-5,6-dicyano-1,4-benzoquinone (10.69 mmol, 2.427 g) in tetrahydrofuran was added dropwise. The reaction was stirred at <10° C. for 1 hour. The reaction was stirred for 2 hours at room temperature. Ethyl acetate was added and the reaction washed with saturated sodium bicarbonate solution. The mixture was passed through a celite plug before being separated. The organic phase was concentrated at reduced pressure to afford the title compound (3.123 g). MS (ESI) m/z 290.3 [M-Boc+H]+

Workup

  1. stirringThe reaction was stirred for 2 hours at room temperature
  2. washthe reaction washed with saturated sodium bicarbonate solution
  3. custombefore being separated
  4. concentrationThe organic phase was concentrated at reduced pressure

Sources & evidence

ORD record
ord-a16927f0a6eb4f1dbb50d2bb20f40fc0
Source dataset
uspto-grants-2015_08
Patent number
US09108939B2

Reaction notes

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