Dimethylformamide → HCID 54093089, compound

HRID 2163125Notes

Reaction equation

HRID 2163125 reaction equation
[CH:1]([CH:3]1[CH:8]([CH3:9])[CH:7]2[CH2:10][CH:4]1[CH2:5][CH2:6]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[CH2:5][CH2:6]2)#[N:12]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 9740Cyanoacetic acidHCID 14923Ammonium HydroxideHCID 551481HCID 551481, compound

Product 1

HCID 54093089HCID 54093089, compoundYield 77%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

A stirred solution of 97 g (0.7 mol) of 2-formyl-3-methylbicyclo[2.2.1]heptane 65 g (0.76 mol) of cyanoacetic acid, 2 ml of ammonium hydroxide (58%), 132 ml of dimethylformamide, and 170 ml benzene was heated to reflux and the water removed with a Dean-Stark trap. The reaction was allowed to continue until the evolution of carbon dioxide ceased (approx. 24 hrs.). Upon completion, the reaction was cooled and the solvent removed under reduced pressure. The residual oil was distilled under vacuum to give 87 g (77% yield) of 2-(2-cyanoethylidene)-3-methylbicyclo[2.2.1]heptane: b.p. 72-85° C/1 mm; ir 2940, 2870, 2220, 1610, 1450, 1380, 830, 740; nmr 0.9-1.1 (3H, m), 1.2-2.8 (9H, m), 2.85-3.2 (2H, m), 4.8-5.4 (1H, m); ms 161.

Workup

  1. temperatureto reflux
  2. customthe water removed with a Dean-Stark trap
  3. custom(approx. 24 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-653fba873cd94c698a0deb8cb13dd394
Source dataset
uspto-grants-1979_01
Patent number
US04132677

Reaction notes

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