Sodium Carbonate → 7-Iodo-1,5-naphthyridine 1-oxide

HRID 509639Notes

Reaction equation

HRID 509639 reaction equation
[I:1][C:2]1[CH:3]=[N:4][C:5]2[C:10]([CH:11]=1)=[N:9][CH:8]=[CH:7][CH:6]=2.ClC1C=C(C=CC=1)C(OO)=[O:17].C(=O)([O-])[O-].[Na+].[Na+]>C(Cl)Cl>[I:1][C:2]1[CH:11]=[C:10]2[C:5]([CH:6]=[CH:7][CH:8]=[N+:9]2[O-:17])=[N:4][CH:3]=1

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 70297m-Chloroperbenzoic acidHCID 497615953-Iodo-1,5-naphthyridine

Product 1

HCID 679930227-Iodo-1,5-naphthyridine 1-oxideYield 54.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 3-iodo-1,5-naphthyridine (D-14) (2.750 g, 10.7 mmol, 1.0 eq) in CH2Cl2 (30 mL), 3-chloroperoxybenzoic acid (2.780 g, 16.1 mmol, 1.5 eq) was added. After the resulting mixture was stirred at RT for 2 h, saturated sodium carbonate solution (50 mL) was added, and extracted with CH2Cl2 (10×30 mL). The combined organic layers were dried over Na2SO4 and filtered. The filtrate was concentrated in vacuo. The resultant residue was purified by silica gel column chromatography (50% EA-PE) to afford the desired product 7-iodo-1,5-naphthyridine 1-oxide (D-15) (1.574 g, 54% yield) as a solid. 1H NMR (400 MHz, CDCl3-d6) δ: 9.45 (dd, J=2.0 Hz, J=0.8 Hz, 1H), 9.18 (d, J=2.5 Hz, 1H), 8.54 (d, J=6.0 Hz, 1H), 7.98 (d, J=8.8 Hz, 1H), 7.59-7.55 (m, 1H); ESI-MS m/z: 272.95 [M+H]+.

Workup

  1. extractionextracted with CH2Cl2 (10×30 mL)
  2. dry with materialThe combined organic layers were dried over Na2SO4
  3. filtrationfiltered
  4. concentrationThe filtrate was concentrated in vacuo
  5. customThe resultant residue was purified by silica gel column chromatography (50% EA-PE)

Sources & evidence

ORD record
ord-44c8ea3f565c4cd789b20ee9e51731dd
Source dataset
uspto-grants-2015_08
Patent number
US09096590B2

Reaction notes

Loading…