Nitric Acid → 4,5-Dimethoxy-2-nitrobenzonitrile

HRID 466994

Reaction equation

HRID 466994 reaction equation
[N+:1]([O-:4])(O)=[O:2].[CH3:5][O:6][C:7]1[CH:8]=[C:9]([CH:12]=[CH:13][C:14]=1[O:15][CH3:16])[C:10]#[N:11]>>[N+:1]([C:12]1[CH:13]=[C:14]([O:15][CH3:16])[C:7]([O:6][CH3:5])=[CH:8][C:9]=1[C:10]#[N:11])([O-:4])=[O:2]

Participants

3

Reactant 2

HCID 944Nitric AcidHCID 748423,4-Dimethoxybenzonitrile

Product 1

HCID 15112884,5-Dimethoxy-2-nitrobenzonitrileYield 98%

Procedure

To a nitric acid (40 mL) in ice bath was added 3,4-dimethoxybenzonitrile (5.0 g, 30.6 mmol) and was allowed to stir for 2 hours. Then the solution was gradually returned to room temperature. To this solution was added ice (200 mL) to get light yellow precipitate which was then collected by filtration to give 6.25 g (98%) of 2-nitro-4,5-dimethoxybenzonitrile. 1H NMR (100 MHz, DMSO-d6): δ3.69 (s, 3H, CH3), 3.90 (s, 3H, CH3), 7.53 (s, 1H, Ar--H), 7.75 (s, 1H, Ar--H). ms: m/z 208 (M+), 192 (M+ -16), 178 (M+ -30), 162 (M+ -46).

Workup

  1. customwas gradually returned to room temperature
  2. customto get light yellow precipitate which
  3. filtrationwas then collected by filtration

Sources & evidence

ORD record
ord-b7c8968b282341dc9153edda70f07640
Source dataset
uspto-grants-1992_10
Patent number
US05158953

Linked notes

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