Hydrochloric Acid → Methyl (p-cyanophenethyl)malonamate

HRID 1647103Notes

Reaction equation

HRID 1647103 reaction equation
[CH3:1][CH:2]([C:6](Cl)=[O:7])[C:3](Cl)=[O:4].NC[CH2:11][C:12]1[CH:19]=[CH:18][C:15]([C:16]#[N:17])=[CH:14][CH:13]=1.C([N:22](CC)CC)C.Cl.C1[CH2:32][O:31]CC1>>[C:16]([C:15]1[CH:18]=[CH:19][C:12]([CH2:11][CH2:1][CH:2]([C:6]([NH2:22])=[O:7])[C:3]([O:31][CH3:32])=[O:4])=[CH:13][CH:14]=1)#[N:17]

Participants

6

Reactant 5

HCID 313Hydrochloric AcidHCID 8028Tetrahydrofuran2×HCID 8471TriethylamineHCID 10931669MethylmalonylchlorideHCID 219125254-(2-Aminoethyl)benzonitrile

Product 1

HCID 54489910Methyl (p-cyanophenethyl)malonamate

Procedure

A solution of 0.59 ml of methyl malonyl chloride in 5 ml of THF was added dropwise at -10° C. to a solution of 731 mg of p-(2-aminoethyl)benzonitrile and 1.39 ml of triethylamine in 10 ml of THF. The mixture was then allowed to warm to room temperature, and was then poured into ice water and adjusted to pH 2 with 1N hydrochloric acid. The THF was evaporated and the aqueous extracts were extracted with ethyl acetate. After drying and concentrating, 380 mg of methyl (p-cyanophenethyl)malonamate, m.p. 125° C., were obtained.

Workup

  1. customThe THF was evaporated
  2. extractionthe aqueous extracts were extracted with ethyl acetate
  3. customAfter drying
  4. concentrationconcentrating

Sources & evidence

ORD record
ord-4af42076eced4de0938d77f3448c992b
Source dataset
uspto-grants-1995_07
Patent number
US05430024

Reaction notes

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