Ammonia → 5-Carbomethoxy-oct-7-enenitrile

HRID 465544Notes

Reaction equation

HRID 465544 reaction equation
C(C1(C(OC)=O)CCCC1=O)C=C.N.[CH3:15][O:16][C:17]([CH:19]([CH2:26][CH:27]=[CH2:28])[CH2:20][CH2:21][CH2:22][C:23]([NH2:25])=O)=[O:18].COC(C(CC=C)CCCC(OC)=O)=O.S(Cl)(Cl)=O>CO>[CH3:15][O:16][C:17]([CH:19]([CH2:26][CH:27]=[CH2:28])[CH2:20][CH2:21][CH2:22][C:23]#[N:25])=[O:18]

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 1100 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-methoxycarbonyl-oct-7-enoic acid amide and methyl 5-methoxycarbonyl-oct-7-enoate. 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 min to 23.6 g of thionyl chloride and the mixture is heated at 80° for 30 min. The reaction mixture is evaporated to dryness under water vacuum and then distilled under high vacuum to yield 5-methoxycarbonyl-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 min
  8. customThe reaction mixture is evaporated to dryness under water vacuum
  9. distillationdistilled under high vacuum

Sources & evidence

ORD record
ord-f4f0ff575f2f4e8f969227d7deedee77
Source dataset
uspto-grants-1992_10
Patent number
US05153214

Reaction notes

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