Hydrochloric Acid → 1,2-Benzenediol, 5-[3-(2,5-dichloro-4,6-diMethyl-3-pyridinyl)-1,2,4-oxadiazol-5-yl]-3-nitro-

HRID 62024Notes

Reaction equation

[Cl:1][C:2]1[C:7]([C:8]2[N:12]=[C:11]([C:13]3[CH:18]=[C:17]([N+:19]([O-:21])=[O:20])[C:16]([OH:22])=[C:15]([O:23]C)[CH:14]=3)[O:10][N:9]=2)=[C:6]([CH3:25])[C:5]([Cl:26])=[C:4]([CH3:27])[N:3]=1.[Cl-].[Al+3].[Cl-].[Cl-].N1C=CC=CC=1.Cl>CN1C(=O)CCC1>[Cl:1][C:2]1[C:7]([C:8]2[N:12]=[C:11]([C:13]3[CH:14]=[C:15]([OH:23])[C:16]([OH:22])=[C:17]([N+:19]([O-:21])=[O:20])[CH:18]=3)[O:10][N:9]=2)=[C:6]([CH3:25])[C:5]([Cl:26])=[C:4]([CH3:27])[N:3]=1

Participants

Conditions

Temperature: 60 °C

Procedure

To an ice-cooled solution of 4-(3-(2,5-dichloro-4,6-dimethylpyridin-3-yl)-1,2,4-oxadiazol-5-yl)-2-methoxy-6-nitrophenol (2.40 g, 5.84 mmol) in NMP (19 mL) was added aluminium chloride (0.977 g, 7.33 mmol) followed by addition of pyridine (1.93 mL). The reaction mixture was heated to 60° C. for 1 hour. It was cooled to room temperature and poured into 2 N HCl-solution (ca. 40 mL). The precipitate was filtered off, washed with water to and dried under vacuum. Recrystallization from acetic acid yielded 1.88 g (81%) of 5-[3-(2,5-dichloro-4,6-dimethylpyridin-3-yl)-[1,2,4]oxadiazol-5-yl]-3-nitrobenzene-1,2-diol.

Workup

temperatureIt was cooled to room temperature
filtrationThe precipitate was filtered off
washwashed with water to and
customdried under vacuum
customRecrystallization from acetic acid

Sources & evidence

ORD record: ord-a1012271537544558cde0150523801e2
Source dataset: uspto-grants-2016_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09446012B2

Reaction notes

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