Potassium Iodide → HCID 19008902, compound

HRID 1742428Notes

Reaction equation

HRID 1742428 reaction equation
[CH2:1]([O:8][C:9]1[CH:10]=[C:11]2[C:16](=[CH:17][CH:18]=1)[C:15]([NH2:19])=[CH:14][CH:13]=[CH:12]2)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].[Na+].Cl[C:23]1[C:28]([N+:29]([O-:31])=[O:30])=[CH:27][CH:26]=[CH:25][N:24]=1.[I-].[K+]>CN(C=O)C.CCOCC>[CH2:1]([O:8][C:9]1[CH:10]=[C:11]2[C:16](=[CH:17][CH:18]=1)[C:15]([NH:19][C:23]1[C:28]([N+:29]([O-:31])=[O:30])=[CH:27][CH:26]=[CH:25][N:24]=1)=[CH:14][CH:13]=[CH:12]2)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

7

Reactant 4

HCID 4875Potassium IodideHCID 24758Sodium hydrideHCID 796132-Chloro-3-nitropyridineHCID 19008956HCID 19008956, compound

Product 1

HCID 19008902HCID 19008902, compound

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
146 °C

Procedure

To a solution of 6-benzyloxy-naphthalen-1-ylamine (4.71 grams, 16.2 mmol) in DMF (25.0 mL) at room temperature was added NaH (372 mg, 16.2 mmol). After 0.5 h, 2-chloro-3-nitropyridine (5.53 grams, 35 mmol) and potassium iodide (2.8 grams, 17 mmol) were added. The reaction mixture was heated at 146° C. for 17 hours. The cooled solution was diluted with ether (300 mL) and the ether solution was washed with saturated aqueous NaCl (2×50 mL). The aqueous solution was extracted with CHCl3 (3×50 mL). The combined extracts were dried (MgSO4) and concentrated in vacuo. The crude residue was chromatographed on SiO2 -gel using a gradient of 20% ethyl acetate/hexanes to 50% ethyl acetate/hexanes to 3.0 grams of a yellow product. 1H NMR (250 MHz, CDCl3): d 8.63 (dd, 1H, J=1.65, 4.8 Hz), 8.58 (dd, 1H, J=1.7, 8.3 Hz), 8.41 (dd, 1H, J=1.73, 4.43 Hz), 8.23 (dd, 1H, J=1.63, 10.2 Hz), 7.93 (d, 1H, J=10 Hz), 7.75 (d, 1H, J=7.32 Hz), 7.68 (d, 1H, J=8.1 Hz), 7.26 (m, 6 H), 6.80 (dd, 1H, J=4.4, 8.1 Hz), 5.25 (s, 2 H).

Workup

  1. washthe ether solution was washed with saturated aqueous NaCl (2×50 mL)
  2. extractionThe aqueous solution was extracted with CHCl3 (3×50 mL)
  3. dry with materialThe combined extracts were dried (MgSO4)
  4. concentrationconcentrated in vacuo
  5. customThe crude residue was chromatographed on SiO2

Sources & evidence

ORD record
ord-120b992753fd4df59c353f310d35be02
Source dataset
uspto-grants-1994_08
Patent number
US05338740

Reaction notes

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