Methyl cyanoacetate → HCID 67390052, compound

HRID 906845Notes

Reaction equation

HRID 906845 reaction equation
[C:1]([CH2:3][C:4]([O:6]C)=O)#[N:2].[CH2:8]([C:10]1[CH:17]=[CH:16][C:13]([CH2:14][NH2:15])=[C:12]([F:18])[CH:11]=1)[CH3:9]>C(O)C.CN(C1C=CN=CC=1)C>[C:1]([CH2:3][C:4]([NH:15][CH2:14][C:13]1[CH:16]=[CH:17][C:10]([CH2:8][CH3:9])=[CH:11][C:12]=1[F:18])=[O:6])#[N:2]

Participants

5

Reactant 2

HCID 7747Methyl cyanoacetateHCID 57531883HCID 57531883, compound

Product 1

HCID 67390052HCID 67390052, compoundYield 40%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 702EthanolSolvent

Conditions

Temperature
60 °C

Procedure

Methyl cyanoacetate (1.16 mL, 13 mmol) and 4-ethyl-2-fluoro-benzylamine (1.15 g, 7.5 mmol) were combined in ethanol (20 mL). 4-(N,N-dimethylamino)pyridine (catalytic) was added and the reaction was heated in a 60° C. oil bath. After 16 hours heating, the reaction was concentrated under reduced pressure to afford crude product which was purified by flash chromatography eluting with a gradient from hexane to 60% ethyl acetate/hexane to afford 2-cyano-N-(4-ethyl-2-fluoro-benzyl)-acetamide (652 mg, 40% yield). 1H-NMR (400 MHz, CDCl3): δ 7.26-7.20 (1H, m), 6.98-6.90 (2H, m), 6.39 (1h, br s), 4.49 (2H, d, J=5.8 Hz), 3.38 (2H, s), 2.64 (2H, q, J=7.6 Hz), 1.23 (3H, t, J=7.6 Hz).

Workup

  1. temperatureAfter 16 hours heating
  2. concentrationthe reaction was concentrated under reduced pressure
  3. customto afford crude product which
  4. customwas purified by flash chromatography
  5. washeluting with a gradient from hexane to 60% ethyl acetate/hexane

Sources & evidence

ORD record
ord-b9899772a83d45d3b3fd6bdb0640d8df
Source dataset
uspto-grants-2011_09
Patent number
US08013001B2

Reaction notes

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