2,3-Dichloro-5,6-dicyano-1,4-benzoquinone → HCID 69270022, compound

HRID 751515Notes

Reaction equation

HRID 751515 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([N:14]2[C:22]3[C:17](=[CH:18][CH:19]=[C:20]([Cl:23])[CH:21]=3)[CH2:16][CH2:15]2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].C(C1C(=O)C(Cl)=C(Cl)C(=O)C=1C#N)#N>O1CCCC1.C(OCC)(=O)C>[C:1]([O:5][C:6]([N:8]1[CH2:9][CH2:10][CH:11]([N:14]2[C:22]3[C:17](=[CH:18][CH:19]=[C:20]([Cl:23])[CH:21]=3)[CH:16]=[CH:15]2)[CH2:12][CH2:13]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 2

HCID 67752,3-Dichloro-5,6-dicyano-1,4-benzoquinoneHCID 69271156HCID 69271156, compound

Product 1

HCID 69270022HCID 69270022, compoundYield 102.3%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
0 °C

Procedure

Dissolve 4-(6-chloro-2,3-dihydroindol-1-yl)-piperidine-1-carboxylic acid tert-butyl ester (3.1 g, 9.2 mmol) in tetrahydrofuran (50 mL) and cool to 0° C. under nitrogen. Dissolve DDQ (2.1 g, 1 eq) in tetrahydrofuran (25 mL) and add dropwise to the reaction over 15 minutes. Stir for 30 minutes at 0° C. Dilute with ethyl acetate then wash with saturated sodium bicarbonate followed by brine. Dry over magnesium sulfate, filter and concentrate to give 3.15 g (102%) crude product. MS (ES, m/z): 279.1 (M+1, product—tert butyl).

Workup

  1. washthen wash with saturated sodium bicarbonate
  2. dry with materialDry over magnesium sulfate
  3. filtrationfilter
  4. concentrationconcentrate

Sources & evidence

ORD record
ord-27ccd57e689a40f1812f3fdd0fb9f4fd
Source dataset
uspto-grants-2008_07
Patent number
US07405305B2

Reaction notes

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