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

HRID 1488679Notes

Reaction equation

HRID 1488679 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-d073af9e2fb649308daa970d15af55a9
Source dataset
uspto-grants-1997_10
Patent number
US05674865

Reaction notes

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