2,3-Dichloro-5,6-dicyano-1,4-benzoquinone → HCID 58505656, compound

HRID 1917614Notes

Reaction equation

[Br-].[Cl:2][C:3]1[CH:8]=[CH:7][C:6]([C:9](=[O:25])[CH2:10][N+:11]2[CH:16]=[CH:15][C:14]([O:17][CH2:18][C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][N:20]=3)=[CH:13][CH:12]=2)=[CH:5][CH:4]=1.[CH3:26][C:27]([CH3:39])([CH3:38])[C:28](=[O:37])[C:29]#[C:30][C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1.C(C1C(=O)C(Cl)=C(Cl)C(=O)C=1C#N)#N>CN(C=O)C>[Cl:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]([C:10]2[N:11]3[C:12]([CH:13]=[C:14]([O:17][CH2:18][C:19]4[CH:24]=[CH:23][CH:22]=[CH:21][N:20]=4)[CH:15]=[CH:16]3)=[C:29]([C:28](=[O:37])[C:27]([CH3:39])([CH3:38])[CH3:26])[C:30]=2[C:31]2[CH:32]=[CH:33][CH:34]=[CH:35][CH:36]=2)=[O:25])=[CH:5][CH:4]=1

Participants

Conditions

Temperature: 70 °C

Procedure

To a suspension of 1-[2-(4-chlorophenyl)-2-oxoethyl]-4-(pyridin-2-ylmethoxy)pyridinium bromide (750 mg, 1.79 mmol) and 4,4-dimethyl-1-phenylpent-1-yn-3-one (333 mg, 1.79 mmol) in DMF (10.0 mL) is added TEA (0.37 mL, 2.68 mmol). The mixture is stirred at 70° C. for 18 h then treated with DDQ (406 mg, 1.79 mmol) and stirred for an additional 1 h. The mixture is then cooled to 23° C. and partitioned between water and EtOAc. The organics are collected, dried with MgSO4, filtered, and concentrated in vacuo. Purification of the crude by flash chromatography (SiO2, hexanes to 50% EtOAc in hexanes) gives the title compound (121 mg, 13%).

Workup

stirringstirred for an additional 1 h
temperatureThe mixture is then cooled to 23° C.
custompartitioned between water and EtOAc
customThe organics are collected
dry with materialdried with MgSO4
filtrationfiltered
concentrationconcentrated in vacuo
customPurification of the crude by flash chromatography (SiO2, hexanes to 50% EtOAc in hexanes)

Sources & evidence

ORD record: ord-37b72b24132944bb9fa67072d1cbc5af
Source dataset: uspto-grants-2013_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08618300B2

Reaction notes

Loading…