Toluene → HCID 86707838, compound

HRID 629045Notes

Reaction equation

HRID 629045 reaction equation
C1(C)C=CC=CC=1.[C:8]([C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=1[C:16]1[N:21]=[CH:20][C:19]([CH2:22][CH:23]([C:28](=O)[CH2:29][CH2:30][CH3:31])[C:24]([O:26][CH3:27])=[O:25])=[CH:18][CH:17]=1)#[N:9].C([O-])(=O)C.[NH4+:37].C(=O)([O-])O.[Na+]>C(O)(=O)C>[NH2:37]/[C:28](/[CH2:29][CH2:30][CH3:31])=[C:23](/[CH2:22][C:19]1[CH:20]=[N:21][C:16]([C:11]2[CH:12]=[CH:13][CH:14]=[CH:15][C:10]=2[C:8]#[N:9])=[CH:17][CH:18]=1)\[C:24]([O:26][CH3:27])=[O:25]

Participants

6

Reactant 4

HCID 1140TolueneHCID 516892Sodium BicarbonateHCID 517165Ammonium AcetateHCID 86707837Methyl 2-{[6-(2-cyanophenyl)pyridin-3-yl]methyl}-3-oxohexanoate

Product 1

HCID 86707838HCID 86707838, compoundYield 95.2%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

Process 2: A toluene (45 mL)-acetic acid (5 mL) mixture containing methyl 2-{[6-(2-cyanophenyl)pyridin-3-yl]methyl}-3-oxohexanoate (1.2 g, 3.6 mmol) and ammonium acetate (8.3 g, 108 mmol) was refluxed under heating for 1 hour. After cooling to room temperature, saturated aqueous solution of sodium hydrogen carbonate was added and extraction was carried out with toluene. After washing with brine, it was dried over anhydrous sodium sulfate and concentrated in vacuo to give methyl (Z)-3-amino-2-{[6-(2-cyanophenyl)pyridin-3-yl]methyl}-2-hexenoate (1.15 g) as brown oil crude product. It was used for the next process without purification.

Workup

  1. temperaturewas refluxed
  2. temperatureunder heating for 1 hour
  3. extractionextraction
  4. washAfter washing with brine, it
  5. dry with materialwas dried over anhydrous sodium sulfate
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-06971f98f25b4a61a7601d72a93b5b74
Source dataset
uspto-grants-2016_04
Patent number
US09315493B2

Reaction notes

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