Nitrogen → HCID 135480, compound

HRID 131108Notes

Reaction equation

HRID 131108 reaction equation
N#N.[C:3]1([CH3:11])[C:4]([CH:9]=O)=[CH:5][CH:6]=[CH:7][CH:8]=1.[C:12]([CH2:14][C:15]([O:17][CH3:18])=[O:16])#[N:13]>C(O)(C)C.N1CCOCC1>[C:12]([C:14](=[CH:9][C:4]1[CH:5]=[CH:6][CH:7]=[CH:8][C:3]=1[CH3:11])[C:15]([O:17][CH3:18])=[O:16])#[N:13]

Participants

6

Reactant 3

HCID 947NitrogenHCID 7747Methyl cyanoacetateHCID 107222-Methylbenzaldehyde

Product 1

HCID 135480HCID 135480, compoundYield 86.3%

Reagents, catalysts & solvents 2

HCID 8083MorpholineCatalystHCID 3776IsopropanolSolvent2×

Procedure

A 100-mL, 1-necked round bottom flask (with magnetic stir-bar and dry N2 adaptor) was charged with 11.6 mL (12.0 g, 100 mmol) of o-tolualdehyde, 8.8 mL (9.9 g, 100 mmol) of methyl cyanoacetate, and 50 mL of isopropanol. Morpholine (0.50 mL, 0.55 g, 6.3 mmol, 6.3 mol %) was added and the mixture was stirred at 20–33° C. for 60 minutes. This mixture was diluted with 25 mL of isopropanol. The precipitate was filtered, washed with 10 mL of isopropanol, and dried to afford 17.37 g (86.3%) of methyl 2-cyano-3-(2-mehtylphenyl)-2-propenoate as a colorless solid.

Workup

  1. filtrationThe precipitate was filtered
  2. washwashed with 10 mL of isopropanol
  3. customdried

Sources & evidence

ORD record
ord-5b1e2c6c98144fec82acbed83173a15c
Source dataset
uspto-grants-2008_06
Patent number
US07384939B2

Reaction notes

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