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

HRID 2199894ノート

反応式

HRID 2199894 の反応式
[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

参加物

5

反応物 3

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

生成物 1

HCID 679930227-Iodo-1,5-naphthyridine 1-oxide収率 54.1%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

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]+.

後処理

  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)

出典と根拠

ORDレコード
ord-c715ffd250c14ed6b94eba85d6ee6380
出典データセット
uspto-grants-2016_06
特許番号
US09359352B2

反応ノート

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