Hydrochloric Acid → 2-Cyano-3-(3,4-dihydroxy-5-nitrophenyl)-N,N-diethylprop-2-enamide

HRID 2354125Notes

Reaction equation

[CH2:1]([N:3]([CH2:22][CH3:23])[C:4](=[O:21])[C:5]([C:19]#[N:20])=[CH:6][C:7]1[CH:12]=[C:11]([N+:13]([O-:15])=[O:14])[C:10]([OH:16])=[C:9]([O:17]C)[CH:8]=1)[CH3:2].C(N(CC)CC)C.[Cl-].[Cl-].[Cl-].[Al+3].Cl>ClCCl>[CH2:22]([N:3]([CH2:1][CH3:2])[C:4](=[O:21])[C:5]([C:19]#[N:20])=[CH:6][C:7]1[CH:12]=[C:11]([N+:13]([O-:15])=[O:14])[C:10]([OH:16])=[C:9]([OH:17])[CH:8]=1)[CH3:23]

Participants

Conditions

Temperature: 2.5 °C

Procedure

A round-bottom flask under nitrogen atmosphere is loaded with N,N-diethyl-2-cyano-3-(-3-methoxy-4-hydroxy-5-nitrophenyl-)-acrylamide (134 g, 0.421 mol) dissolved in dichloromethane (0.65 l) and triethylamine (128 g, 1.26 mol). The solution is cooled to 0-5° C. and aluminium trichloride (67.4 g, 0.505 mol) is added in portions. After that, the mixture is refluxed for 3-4 hours, until completion of the conversion. The reaction mixture is cooled to 0-5° C., a 20% hydrochloric acid solution (0.5 l) is dropped in the mixture, which is left under stirring at room temperature for 30 minutes. The resulting solid is filtered, washing with water (0.1 l×3), and dried in a static dryer under reduced pressure at 50° C.; 126 g are obtained. Yield: 98%.

Workup

temperatureAfter that, the mixture is refluxed for 3-4 hours, until completion of the conversion
temperatureThe reaction mixture is cooled to 0-5° C.
waitis left
filtrationThe resulting solid is filtered
washwashing with water (0.1 l×3)
customdried in a static dryer under reduced pressure at 50° C.
custom126 g are obtained

Sources & evidence

ORD record: ord-33cc1b1e47c64f6395eff947ab093315
Source dataset: uspto-grants-2010_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07750177B2

Reaction notes

Loading…