Sodium Bicarbonate → 2-Cyano-3-cyclobutyloxy-4,5-dimethoxynitrobenzene

HRID 1004020Notes

Reaction equation

HRID 1004020 reaction equation
F[B-](F)(F)F.[O:6]=[N+:7]=[O:8].[CH:9]1([O:13][C:14]2[C:21]([O:22][CH3:23])=[C:20]([O:24][CH3:25])[CH:19]=[CH:18][C:15]=2[C:16]#[N:17])[CH2:12][CH2:11][CH2:10]1.C(=O)(O)[O-].[Na+]>C(#N)C>[C:16]([C:15]1[C:14]([O:13][CH:9]2[CH2:12][CH2:11][CH2:10]2)=[C:21]([O:22][CH3:23])[C:20]([O:24][CH3:25])=[CH:19][C:18]=1[N+:7]([O-:8])=[O:6])#[N:17]

Participants

5

Reactant 3

HCID 516892Sodium BicarbonateHCID 11073463Nitronium tetrafluoroborateHCID 184706162-Cyclobutyloxy-3,4-dimethoxybenzonitrile

Product 1

HCID 184706322-Cyano-3-cyclobutyloxy-4,5-dimethoxynitrobenzeneYield 53.4%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

Nitronium tetrafluoroborate (4.64 g, 0.035 mol) was added portionwise to an ice cooled solution of 2-cyclobutyloxy-3,4-dimethoxybenzonitrile (6.28 g, 0.027 mol) in acetonitrile (150 ml) and the reaction stirred for 1 hour. Saturated aqueous sodium bicarbonate solution (150 ml) was added and the mixture extracted with ethyl acetate (400 ml). The combined organic extracts were washed with water (150 ml), dried (MgSO4), filtered and evaporated under reduced pressure to give a dark brown oil. The crude product was purified on silica gel eluting with dichloromethane to give the subtitle compound as a pale yellow solid (4.01 g, 53%). Rf 0.23 (hexane:isopropyl alcohol:0.880 aqueous ammonia 90:10:0.75, v/v). MS m/z 296 (MNH4)+.

Workup

  1. extractionthe mixture extracted with ethyl acetate (400 ml)
  2. washThe combined organic extracts were washed with water (150 ml)
  3. dry with materialdried (MgSO4)
  4. filtrationfiltered
  5. customevaporated under reduced pressure
  6. customto give a dark brown oil
  7. customThe crude product was purified on silica gel eluting with dichloromethane

Sources & evidence

ORD record
ord-07b0b4e5133c4eb58578c93518ff1df2
Source dataset
uspto-grants-2000_04
Patent number
US06048864

Reaction notes

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