Ammonia → 5-Carbomethoxy-oct-7-enenitrile

HRID 1494089Notes

Reaction equation

HRID 1494089 reaction equation
C(C1(C(OC)=O)CCCC1=O)C=C.N.[C:15]([CH:19]([CH2:26][CH:27]=[CH2:28])[CH2:20][CH2:21][CH2:22][C:23]([NH2:25])=O)([O:17][CH3:18])=[O:16].C(C(CC=C)CCCC(OC)=O)(OC)=O.S(Cl)(Cl)=O>CO>[C:15]([CH:19]([CH2:26][CH:27]=[CH2:28])[CH2:20][CH2:21][CH2:22][C:23]#[N:25])([O:17][CH3:18])=[O:16]

Participants

7

Reactant 5

HCID 222Ammonia2×HCID 24386Thionyl ChlorideHCID 10081040HCID 10081040, compoundHCID 14986661HCID 14986661, compoundHCID 14986662Methyl 5-methoxycarbonyl-oct-7-enoate

Product 1

HCID 149867035-Carbomethoxy-oct-7-enenitrile

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Methyl 1-allyl-2-oxocyclopentane-1-carboxylate (1.1 Kg) is added to 1,100 mL of methanol previously saturated with ammonia gas at ice bath temperature. The reaction mixture is stirred first at ice bath temperature and then at room temperature overnight with constant introduction of ammonia. The reaction mixture is evaporated to dryness to yield starting material and a mixture of 5-carbomethoxyoct-7-enoic acid amide and methyl 5-carbomethoxy-oct-7enoate. The residue is distilled under reduced pressure to yield a mixture of the diester and ester amide. A portion (25 g) is added dropwise over 40 minutes to 23.6 g of thionyl chloride and the mixture is heated at 80° for 30 minutes. The reaction mixture is evaporated to dryness under water vacuum and then distilled under high vacuum to yield 5-carbomethoxy-oct-7-enenitrile.

Workup

  1. customat room temperature
  2. customovernight
  3. customThe reaction mixture is evaporated to dryness
  4. customto yield
  5. distillationThe residue is distilled under reduced pressure
  6. customto yield
  7. temperaturethe mixture is heated at 80° for 30 minutes
  8. customThe reaction mixture is evaporated to dryness under water vacuum
  9. distillationdistilled under high vacuum

Sources & evidence

ORD record
ord-04d4bf0d781844c98d76519c4eba0fca
Source dataset
uspto-grants-1991_06
Patent number
US05025025

Reaction notes

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