2,3-Dichloro-5,6-dicyano-1,4-benzoquinone → HCID 118598829, compound

HRID 1050391Notes

Reaction equation

HRID 1050391 reaction equation
COC1C=CC(C[O:8][C:9]2[C:14](=[O:15])[N:13]3[C:16]4([CH2:24][CH2:23][CH2:22][CH2:21][CH2:20]4)[NH:17][C:18](=[O:19])[C:12]3=[C:11]([CH3:25])[CH:10]=2)=CC=1.ClC1C(=O)C(C#N)=C(C#N)C(=O)C=1Cl>ClCCl>[OH:8][C:9]1[C:14](=[O:15])[N:13]2[C:16]3([CH2:24][CH2:23][CH2:22][CH2:21][CH2:20]3)[NH:17][C:18](=[O:19])[C:12]2=[C:11]([CH3:25])[CH:10]=1

Participants

4

Reactant 2

HCID 67752,3-Dichloro-5,6-dicyano-1,4-benzoquinoneHCID 118598862HCID 118598862, compound

Product 1

HCID 118598829HCID 118598829, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 6′-((4-methoxybenzyl)oxy)-8′-methyl-2′H-spiro[cyclohexane-1,3′-imidazo[1,5-a]pyridine]-1′,5′-dione (2, 1.5 g, 4.07 mmol) in dichloromethane (20 mL) is added 2,3-dichloro-5,6-dicyano-p-benzoquinone (1.38 g, 6.10 mmol). The reaction is stirred at room temperature for 2 h. The resulting mixture is concentrated and purified via column chromatography to afford 6′-hydroxy-8′-methyl-2′H-spiro[cyclohexane-1,3′-imidazo[1,5-a]pyridine]-1′,5′-dione (3).

Workup

  1. concentrationThe resulting mixture is concentrated
  2. custompurified via column chromatography

Sources & evidence

ORD record
ord-48a026e318c64a3b82a9084b378bab10
Source dataset
uspto-grants-2016_07
Patent number
US09382248B2

Reaction notes

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