Acetic Acid → HCID 90410893, compound

HRID 717378Notes

Reaction equation

[CH2:1]([O:8][C:9]1[C:16]([N:17]([CH3:19])[CH3:18])=[CH:15][CH:14]=[CH:13][C:10]=1[CH:11]=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(O)(=O)C.CC(O)=O.N.[N+:29]([CH3:32])([O-:31])=[O:30]>C(OCC)(=O)C>[CH2:1]([O:8][C:9]1[C:10](/[CH:11]=[CH:32]\[N+:29]([O-:31])=[O:30])=[CH:13][CH:14]=[CH:15][C:16]=1[N:17]([CH3:19])[CH3:18])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

Conditions

Temperature: 105 °C

Procedure

Into a 100-mL 3-necked round-bottom flask purged and maintained with an inert atmosphere of nitrogen, was placed 2-(benzyloxy)-3-(dimethylamino)benzaldehyde (5 g, 19.58 mmol, 1.00 equiv), acetic acid (40 mL), acetic acid amine (750 mg, 9.73 mmol, 0.50 equiv) and nitromethane (11.96 g, 195.94 mmol, 10.01 equiv). The resulting solution was stirred overnight at 105° C. in an oil bath. The resulting solution was diluted with 200 mL of ethyl acetate. The mixture was washed with NaOH (5 mol/L) until pH=7. The mixture was dried over anhydrous sodium sulfate and concentrated under vacuum. The residue was applied onto a silica gel column with ethyl acetate/petroleum ether (1:20). This resulted in 3.5 g (60%) of 2-(benzyloxy)-N,N-dimethyl-3-[(Z)-2-nitroethenyl]aniline as a dark red solid. MS (ESI) m/z 299 ([M+H]+).

Workup

customInto a 100-mL 3-necked round-bottom flask purged
temperaturemaintained with an inert atmosphere of nitrogen
washThe mixture was washed with NaOH (5 mol/L) until pH=7
dry with materialThe mixture was dried over anhydrous sodium sulfate
concentrationconcentrated under vacuum
customThis resulted in 3.5 g (60%) of 2-(benzyloxy)-N,N-dimethyl-3-[(Z)-2-nitroethenyl]aniline as a dark red solid

Sources & evidence

ORD record: ord-19ca4c91f3154675b9292818fa81fa61
Source dataset: uspto-grants-2015_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09193707B2

Reaction notes

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