Dimethylformamide dimethyl acetal → HCID 178488756, compound

HRID 506149Notes

Reaction equation

[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH2:11][C:12](=[O:16])[CH2:13][C:14]#[N:15])[CH:6]=[CH:7][C:8]=1[O:9][CH3:10].CO[CH:19](OC)[N:20](C)C.[C:25]([O-])(=O)C.[NH4+]>CN(C=O)C.CCO>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:11]2[CH:25]=[N:15][CH:14]=[C:13]([C:12]=2[OH:16])[C:19]#[N:20])[CH:6]=[CH:7][C:8]=1[O:9][CH3:10]

Participants

Conditions

Temperature: 122 °C

Procedure

To a solution of 4-(3,4-dimethoxyphenyl)-3-oxo-butyronitrile (5.0 g, 23 mmol) in DMF (12 mL) was added dimethylformamide-dimethylacetal (DMF-DMA, 13.5 mL, 101 mmol) and the solution heated at 122° C. overnight. Concentration on a rotary evaporator under high vacuum gave an orange-red solid. This solid was dissolved in EtOH (100 mL) and excess ammonium acetate was added and the reaction mixture was heated at 85° C. for 1 h. The reaction mixture was allowed to cool to room temperature (r.t.) for 1 h then the solids were collected by filtration and washed with EtOH (cold) to give 5-(3,4-dimethoxyphenyl)-4-hydroxynicotinonitrile (4.1 g, 69%) as a brown solid. The filtrate was concentrated on a rotary evaporator and the residue purified on silica gel with 0-25% MeOH in CH2Cl2 to give an additional amount of 5-(3,4-dimethoxyphenyl)-4-hydroxynicotinonitrile.

Workup

concentrationConcentration
customon a rotary evaporator under high vacuum
customgave an orange-red solid
temperaturethe reaction mixture was heated at 85° C. for 1 h
temperatureto cool to room temperature (r.t.) for 1 h
filtrationthe solids were collected by filtration
washwashed with EtOH (cold)

Sources & evidence

ORD record: ord-8aff3a530c384a6ea1b8ab1541be8509
Source dataset: uspto-grants-2010_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07781591B2

Reaction notes

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