Ethyl Acetate → HCID 61028432, compound

HRID 1629119Notes

Reaction equation

HRID 1629119 reaction equation
C(OCC)(=O)C.[N+:7]([C:10]1[CH:20]=[CH:19][CH:18]=[CH:17][C:11]=1[O:12][CH2:13][CH2:14][C:15]#[N:16])([O-])=O.[H][H]>[Pd]>[NH2:7][C:10]1[CH:20]=[CH:19][CH:18]=[CH:17][C:11]=1[O:12][CH2:13][CH2:14][C:15]#[N:16]

Participants

5

Reactant 3

HCID 8857Ethyl AcetateHCID 14916233HCID 14916233, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 61028432HCID 61028432, compoundYield 98%

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Procedure

To palladium (0.00748 g, 0.0702 mmol) in a 50 mL flask with stirbar was added ethyl acetate (11.7 g, 133 mmol) under nitrogen, and then nitrile 83 (0.675 g, 3.51 mmol) was added (FIG. 18). The flask was fitted with a balloon containing hydrogen, and the nitrogen inlet was removed. The reaction was stirred vigorously for 4 hours, and then was filtered through celite, washing with ethyl acetate. The product 84 required no further purification, 98% yield. 1H NMR (500 MHz, CDCl3) δ 6.85-6.77 (m, 1H), 6.74-6.62 (m, 3H), 4.08 (t, J=6.1 Hz, 2H), 3.94-3.74 (m, 2H), 2.72 (t, J=6.1 Hz, 2H). LRMS m/z Calcd. for C9H10N2O: 162.07931, found: 163.1 [M+1].

Workup

  1. customThe flask was fitted with a balloon
  2. customthe nitrogen inlet was removed
  3. filtrationwas filtered through celite
  4. washwashing with ethyl acetate
  5. customno further purification, 98% yield

Sources & evidence

ORD record
ord-251996c216594dc6b185cb589a387290
Source dataset
uspto-grants-2014_07
Patent number
US08785626B2

Reaction notes

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