Dimethylformamide → HCID 54023491, compound

HRID 2163122Notes

Reaction equation

HRID 2163122 reaction equation
[CH:1]([CH:3]1[CH:8]([CH3:9])[CH:7]2[CH2:10][CH:4]1[CH:5]=[CH:6]2)=O.[C:11]([CH2:13]C(O)=O)#[N:12].[OH-].[NH4+].CN(C)C=O>C1C=CC=CC=1>[C:11]([CH2:13][CH:1]=[C:3]1[CH:8]([CH3:9])[CH:7]2[CH2:10][CH:4]1[CH:5]=[CH:6]2)#[N:12]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 9740Cyanoacetic acidHCID 14923Ammonium HydroxideHCID 1108583-Methylbicyclo[2.2.1]hept-5-ene-2-carbaldehyde

Product 1

HCID 54023491HCID 54023491, compoundYield 75.5%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

A stirred solution of 136 g (1.0 mole) of 2-formyl-3-methylbicyclo[2.2.1]hept-5ene, 91 g (1.05 mol) of cyanoacetic acid, 3 g (0.05 mol) of ammonium hydroxide (58%), 132 ml of dimethylformamide, and 170 ml of benzene was heated to reflux and the water removed with a Dean-Stark trap. The reaction was allowed to continue until the carbon dioxide evolution ceased (approx. 31 hrs). Upon completion, the reaction was cooled and the solvent removed under reduced pressure. The residual oil was distilled under vacuum to give 120 g (75.5% yield) of 2(2-cyanoethylidene)-3-methylbicyclo[2.2.1]hept-5-ene: b.p. 70-80° C/1 mm; nD20 1.5080; ir 3060, 2250, 1460, 1380, 760, 740, 726, 700; nmr 1.15 (3H, d, J=7 Hz, methyl), 4.9-5.5 (1H, m, vinyl H), 5.7-6.1 (2H; m, vinyl H); ms 159.

Workup

  1. temperatureto reflux
  2. customthe water removed with a Dean-Stark trap
  3. custom(approx. 31 hrs)
  4. temperatureUpon completion, the reaction was cooled
  5. customthe solvent removed under reduced pressure
  6. distillationThe residual oil was distilled under vacuum

Sources & evidence

ORD record
ord-c037b12e255e40efaea2dba9e8f3b5d9
Source dataset
uspto-grants-1979_01
Patent number
US04132677

Reaction notes

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