Dimethylformamide → 5-(4-Cyanobenzyloxy)-2-nitrobenzaldehyde

HRID 865346Notes

Reaction equation

HRID 865346 reaction equation
[OH:1][C:2]1[CH:3]=[CH:4][C:5]([N+:10]([O-:12])=[O:11])=[C:6]([CH:9]=1)[CH:7]=[O:8].C(=O)([O-])[O-].[K+].[K+].C[N:20]([CH3:23])C=O>>[C:23]([C:3]1[CH:2]=[CH:9][C:6]([CH2:7][O:1][C:2]2[CH:3]=[CH:4][C:5]([N+:10]([O-:12])=[O:11])=[C:6]([CH:9]=2)[CH:7]=[O:8])=[CH:5][CH:4]=1)#[N:20]

Participants

4

Reactant 3

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 392115-Hydroxy-2-nitrobenzaldehyde

Product 1

HCID 229049735-(4-Cyanobenzyloxy)-2-nitrobenzaldehydeYield 82%

Conditions

Temperature
50 °C

Procedure

To a stirred solution of 10.0 g (59.8 mmol) of 5-hydroxy-2-nitrobenzaldehyde and 12.3 g (62.8 mmol) of a-bromo-p-tolylnitrile in 50 ml of dry dimethyl-formamide was added 9.10 g (65.8 g) of anhydrous potassium carbonate. The mixture was warmed to 50° C. for 2 h and partitioned between water and ethyl acetate. The organic phase was washed with 1N sodium bicarbonate, water, brine, and dried over anhydrous magnesium sulfate. Concentration gave 13.8 g (82%) of 5-(4-cyanobenzyloxy)-2-nitrobenzaldehyde. 1H NMR (300 MHz, d6 -acetone) d 10.39 (1H, s, Ar-CHO), 8.23 (1H, d, J=9.0 Hz, O-Ar-H), 7.85 (2H, d, J=8.3 Hz, NC-Ar-H2), 7.77 (2H, d, J=8.3 Hz, NC-Ar-H2), 7.48 (1H, dd, J=9.0, 2.9 Hz, O-Ar-H), 7.43 (1H, d, J=2.9 Hz, O-Ar-H), 5.50 (2H, s, ArCH2O).

Workup

  1. custompartitioned between water and ethyl acetate
  2. washThe organic phase was washed with 1N sodium bicarbonate, water, brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationConcentration

Sources & evidence

ORD record
ord-42856b0d7bd043c094f0eb35418fb58e
Source dataset
uspto-grants-1996_10
Patent number
US05565449

Reaction notes

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