Sodium Cyanide → 1-(4-(Pyridin-4-yloxy)phenylamino)-cyclobutanecarbonitrile

HRID 515799Notes

Reaction equation

HRID 515799 reaction equation
[C-:1]#[N:2].[Na+].[N:4]1[CH:9]=[CH:8][C:7]([O:10][C:11]2[CH:17]=[CH:16][C:14]([NH2:15])=[CH:13][CH:12]=2)=[CH:6][CH:5]=1.[C:18]1(=O)[CH2:21][CH2:20][CH2:19]1>CC(O)=O>[N:4]1[CH:5]=[CH:6][C:7]([O:10][C:11]2[CH:17]=[CH:16][C:14]([NH:15][C:18]3([C:1]#[N:2])[CH2:21][CH2:20][CH2:19]3)=[CH:13][CH:12]=2)=[CH:8][CH:9]=1

Participants

5

Reactant 3

HCID 8929Sodium CyanideHCID 14496CyclobutanoneHCID 115645894-(Pyridin-4-yloxy)aniline

Product 1

HCID 673748051-(4-(Pyridin-4-yloxy)phenylamino)-cyclobutanecarbonitrileYield 65%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

Sodium cyanide (395 mg, 8.06 mmol) was added to a mixture of 4-(pyridin-4-yloxy)aniline (500 mg, 2.69 mmol) and cyclobutanone (376 mg, 5.37 mmol) in AcOH (99%, 6 mL) in a microwave vial. The reaction mixture was irradiated with microwaves (Biotage) at 120° C. for 30 min. The slightly yellowish solution was concentrated to dryness. The residue was diluted with water and extracted with EtOAc (2×). The combined organic layers were dried over MgSO4 and concentrated to dryness to afford 463 mg (65%) of 1-(4-(pyridin-4-yloxy)phenylamino)-cyclobutanecarbonitrile as a yellow oil. 1H NMR (400 MHz, CDCl3) δ 8.46-8.38 (m, 2H), 7.02-6.94 (m, 2H), 6.79 (m, 2H), 6.72-6.64 (m, 2H), 2.86-2.74 (m, 2H), 2.46-2.34 (m, 2H), 2.22 (m, 2H)

Workup

  1. customThe reaction mixture was irradiated with microwaves (Biotage) at 120° C. for 30 min
  2. concentrationThe slightly yellowish solution was concentrated to dryness
  3. additionThe residue was diluted with water
  4. extractionextracted with EtOAc (2×)
  5. dry with materialThe combined organic layers were dried over MgSO4
  6. concentrationconcentrated to dryness

Sources & evidence

ORD record
ord-7b408df272a0413aab6bd93323467c4f
Source dataset
uspto-grants-2015_08
Patent number
US09108944B2

Reaction notes

Loading…