2,3-Dichloro-5,6-dicyano-1,4-benzoquinone → HCID 18427649, compound

HRID 863136Notes

Reaction equation

HRID 863136 reaction equation
[CH2:1]([O:8][C:9]1[CH:10]=[C:11]2[C:15](=[CH:16][CH:17]=1)[CH:14]([C:18]1[CH:23]=[CH:22][C:21]3[O:24][CH2:25][O:26][C:20]=3[CH:19]=1)[CH:13]([C:27]([O:29][CH3:30])=[O:28])[C:12]2=[O:31])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.ClC1C(=O)C(C#N)=C(C#N)C(=O)C=1Cl>C1C=CC=CC=1>[CH2:1]([O:8][C:9]1[CH:10]=[C:11]2[C:15](=[CH:16][CH:17]=1)[C:14]([C:18]1[CH:23]=[CH:22][C:21]3[O:24][CH2:25][O:26][C:20]=3[CH:19]=1)=[C:13]([C:27]([O:29][CH3:30])=[O:28])[C:12]2=[O:31])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 67752,3-Dichloro-5,6-dicyano-1,4-benzoquinoneHCID 18427661HCID 18427661, compound

Product 1

HCID 18427649HCID 18427649, compoundYield 60.3%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of methyl 5-benzyloxy-1-(3,4-methylenedioxyphenyl)-3-oxoindane-2-carboxylate (27.3 g, 65.6 mmol) in benzene (90 ml), cooled in an ice-H2O bath, was added 2,3-dichloro-5,6-dicyano-1,4-benzoquinone (15.4 g, 67.8 mmol). The resulting mixture was stirred at 0° C. for 1 h, allowed to warm to room temperature for 1.5 h, and finally warmed to 40° C. for 1 h. The solid which formed was removed by filtration and washed with benzene. The combined filtrate and washings were poured into EtOAc (200 ml) and washed successively with aqueous Na2CO3 (3×), H2O (3×), 3M HCl, H2O (3×) and saturated aqueous NaCl and dried. The solvent was removed in vacuo, and the residue was crystallized from EtOAc/hexanes to afford the title compound (16.4 g, 60%) as a red crystalline solid; m.p. 140°-141° C.

Workup

  1. temperatureto warm to room temperature for 1.5 h
  2. temperaturefinally warmed to 40° C. for 1 h
  3. customThe solid which formed
  4. customwas removed by filtration
  5. washwashed with benzene
  6. additionThe combined filtrate and washings were poured into EtOAc (200 ml)
  7. washwashed successively with aqueous Na2CO3 (3×), H2O (3×), 3M HCl, H2O (3×) and saturated aqueous NaCl
  8. customdried
  9. customThe solvent was removed in vacuo
  10. customthe residue was crystallized from EtOAc/hexanes

Sources & evidence

ORD record
ord-14da50c2558c463b9222f28b0c2b5ffb
Source dataset
uspto-grants-1998_02
Patent number
US05719183

Reaction notes

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