2,3-Dichloro-5,6-dicyano-1,4-benzoquinone → HCID 58154662, compound

HRID 2359424Notes

Reaction equation

HRID 2359424 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([CH:7]2[NH:16][CH2:15][C:14]3[C:9](=[C:10]([C:17]([O:19][CH3:20])=[O:18])[CH:11]=[CH:12][CH:13]=3)[NH:8]2)[CH:2]=1.C(C1C(=O)C(Cl)=C(Cl)C(=O)C=1C#N)#N>C(Cl)Cl>[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([C:7]2[N:16]=[CH:15][C:14]3[C:9](=[C:10]([C:17]([O:19][CH3:20])=[O:18])[CH:11]=[CH:12][CH:13]=3)[N:8]=2)[CH:2]=1

Participants

4

Reactant 2

HCID 67752,3-Dichloro-5,6-dicyano-1,4-benzoquinoneHCID 58154538HCID 58154538, compound

Product 1

HCID 58154662HCID 58154662, compoundYield 89.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of methyl 2-(pyridin-3-yl)-1,2,3,4-tetrahydroquinazoline-8-carboxylate (4.0 g, 14.8 mmol) and DDQ (5.0 g, 22.2 mmol) in CH2Cl2 (50 mL) was stirred at room temperature for 24 hours. The solvent was removed in vacuo, and the residue was purified by silica gel column chromatography (5% methanol in CH2Cl2) to obtain methyl 2-(pyridin-3-yl)quinazoline-8-carboxylate (3.5 g, 89% yield).

Workup

  1. customThe solvent was removed in vacuo
  2. customthe residue was purified by silica gel column chromatography (5% methanol in CH2Cl2)

Sources & evidence

ORD record
ord-d690389701164eaa817ce1ef9732c9b0
Source dataset
uspto-grants-2014_04
Patent number
US08685970B2

Reaction notes

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