2-Nitropropane → HCID 13588605, compound

HRID 1285519Notes

Reaction equation

HRID 1285519 reaction equation
[C:1](/[C:3](=[CH:9]\[C:10]1[CH:15]=[CH:14][C:13]([CH3:16])=[CH:12][CH:11]=1)/[C:4]([O:6][CH2:7][CH3:8])=[O:5])#[N:2].[C:17]([CH2:19][C:20](OCC)=O)#N.C1(C)C=CC(C=O)=CC=1.[N+](C(C)C)([O-])=O.C(=O)([O-])[O-].[K+].[K+]>C(O)C>[C:1]([C:3]1([C:4]([O:6][CH2:7][CH3:8])=[O:5])[CH:9]([C:10]2[CH:11]=[CH:12][C:13]([CH3:16])=[CH:14][CH:15]=2)[C:19]1([CH3:20])[CH3:17])#[N:2]

Participants

7

Reactant 5

HCID 3982-NitropropaneHCID 77254-MethylbenzaldehydeHCID 7764Ethyl cyanoacetateHCID 11430Potassium CarbonateHCID 682087Ethyl (2E)-2-cyano-3-(4-methylphenyl)-2-propenoate

Product 1

HCID 13588605HCID 13588605, compoundYield 74%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 576 mg (2.68 mmoles) of (E)-ethyl 2-cyano-3-(p-methylphenyl)-2-propenoate (7) [prepared from ethyl cyanoacetate and p-tolualdehyde (p-methylbenzaldehyde) using the procedure described in Example I for an analogous cyanoester], 0.25 ml (2.78 mmoles) of 2-nitropropane, 398 mg (2.88 mmoles) of anhydrous potassium carbonate, and 2.0 ml of absolute ethanol was heated at reflux for 7 hours. The product was isolated as described in the procedure of Example VIII, affording 511 mg (74% yield) of cyclopropanoid cyanoester 15: bp: 155°-183° C. (bath temperature, 0.15 mm).

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 7 hours
  3. customThe product was isolated

Sources & evidence

ORD record
ord-40ad7701beb841989d498e25074bbf07
Source dataset
uspto-grants-1986_01
Patent number
US04567265

Reaction notes

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