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

HRID 42677Notes

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 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
customdried under vacuum
customRecrystallization from acetic acid

Sources & evidence

ORD record: ord-86c5393a77b044ada0318eaa2cb613ad
Source dataset: uspto-grants-2013_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08536203B2

Reaction notes

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