Hydrochloric Acid → (Z)-3-(3,4-dihydroxy-5-nitrophenyl)-2-(6-(trifluoromethyl)pyridin-3-yl)acrylonitrile

HRID 61994Notes

Reaction equation

[OH:1][C:2]1[C:7]([N+:8]([O-:10])=[O:9])=[CH:6][C:5](/[CH:11]=[C:12](/[C:15]2[CH:16]=[N:17][C:18]([C:21]([F:24])([F:23])[F:22])=[CH:19][CH:20]=2)\[C:13]#[N:14])=[CH:4][C:3]=1[O:25]C.[Cl-].[Al+3].[Cl-].[Cl-].N1C=CC=CC=1.Cl>ClCCCl>[OH:25][C:3]1[CH:4]=[C:5](/[CH:11]=[C:12](/[C:15]2[CH:16]=[N:17][C:18]([C:21]([F:24])([F:22])[F:23])=[CH:19][CH:20]=2)\[C:13]#[N:14])[CH:6]=[C:7]([N+:8]([O-:10])=[O:9])[C:2]=1[OH:1]

Participants

Conditions

Temperature: 80 °C

Procedure

To a stirred solution of (Z)-3-(4-hydroxy-3-methoxy-5-nitrophenyl)-2-(6-(trifluoromethyl)pyridin-3-yl)acrylonitrile (0.526 g, 1.44 mmol) in 1,2-dichloroethane (10 mL) cooled in an ice-water bath was added aluminium chloride (0.24 g, 1.80 mmol) in one portion followed by pyridine (0.46 g, 5.77 mmol) dropwise. The resulting red suspension was stirred at 80° C. for two hours, then cooled to room temperature and poured onto cold 2 N aqueous hydrochloric acid (100 mL). The precipitate was filtered off, washed with water and dried to give (Z)-3-(3,4-dihydroxy-5-nitrophenyl)-2-(6-(trifluoromethyl)pyridin-3-yl)acrylonitrile, 0.308 g (61%)

Workup

temperaturecooled to room temperature
filtrationThe precipitate was filtered off
washwashed with water
customdried

Sources & evidence

ORD record: ord-5fcacd8cfa484b30b085efb63c55dc7b
Source dataset: uspto-grants-2016_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09446012B2

Reaction notes

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