2,3-Dichloro-5,6-dicyano-1,4-benzoquinone → HCID 46840742, compound

HRID 1846268Notes

Reaction equation

HRID 1846268 reaction equation
[CH:1]([C:5]1[CH:10]=[CH:9][C:8]([N:11]2[C:20](=[O:21])[C:19]3[C:14](=[CH:15][C:16]([F:22])=[CH:17][CH:18]=3)[NH:13][CH:12]2[C:23]2[CH:28]=[C:27]([CH3:29])[C:26]([O:30][CH2:31][CH2:32][OH:33])=[C:25]([CH3:34])[CH:24]=2)=[CH:7][CH:6]=1)([CH2:3][CH3:4])[CH3:2].C(C1C(=O)C(Cl)=C(Cl)C(=O)C=1C#N)#N>C1COCC1>[CH:1]([C:5]1[CH:10]=[CH:9][C:8]([N:11]2[C:20](=[O:21])[C:19]3[C:14](=[CH:15][C:16]([F:22])=[CH:17][CH:18]=3)[N:13]=[C:12]2[C:23]2[CH:28]=[C:27]([CH3:29])[C:26]([O:30][CH2:31][CH2:32][OH:33])=[C:25]([CH3:34])[CH:24]=2)=[CH:7][CH:6]=1)([CH2:3][CH3:4])[CH3:2]

Participants

4

Reactant 2

HCID 67752,3-Dichloro-5,6-dicyano-1,4-benzoquinoneHCID 70876732HCID 70876732, compound

Product 1

HCID 46840742HCID 46840742, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 3-(4-sec-butyl-phenyl)-7-fluoro-2-[4-(2-hydroxy-ethoxy)-3,5-dimethyl-phenyl]-2,3-dihydro-1H-quinazolin-4-one (0.11 g, 0.24 mmol) in anhydrous THF (30 mL) was added DDQ (0.09 g, 0.4 mmol) and the reaction mixture was stirred for 72 hours at room temperature. The solvent was evaporated in vacuo and the crude material was purified by column chromatography (silica gel; 230-400 mesh; 0.5% methanol/CH2Cl2 as eluent) to give the title compound (Q) as white solid. Yield: 0.06 g (50%). MP 53.9-54.4° C. 1H-NMR (400 MHz, CDCl3): δ 8.38 (dd, 1H), 7.43 (dd, 1H), 7.22-7.05 (m, 5H), 6.99 (s, 2H), 3.90 (m, 2H), 3.78 (m, 2H), 2.59 (m, 1H), 2.16 (s, 6H), 2.05 (t, 1H), 1.59 (m, 2H), 1.20 (d, 3H), 0.71 (t, 3H).

Workup

  1. customThe solvent was evaporated in vacuo
  2. customthe crude material was purified by column chromatography (silica gel; 230-400 mesh; 0.5% methanol/CH2Cl2 as eluent)

Sources & evidence

ORD record
ord-cd7ac15ea5bd40d2ab4a7f7d0d6e3386
Source dataset
uspto-grants-2015_02
Patent number
US08952021B2

Reaction notes

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