Iodine → Methyl 6-amino-5-iodo-2-methylnicotinate

HRID 526006ノート

反応式

HRID 526006 の反応式
I([O-])(=O)(=O)=O.[Na+].[I:7]I.[NH2:9][C:10]1[CH:19]=[CH:18][C:13]([C:14]([O:16][CH3:17])=[O:15])=[C:12]([CH3:20])[N:11]=1.S([O-])([O-])(=O)=S.[Na+].[Na+]>CN(C=O)C.O>[NH2:9][C:10]1[C:19]([I:7])=[CH:18][C:13]([C:14]([O:16][CH3:17])=[O:15])=[C:12]([CH3:20])[N:11]=1

参加物

7

反応物 4

HCID 807IodineHCID 24477Sodium ThiosulfateHCID 23667635Sodium periodateHCID 55252884Methyl 6-amino-2-methylpyridine-3-carboxylate

生成物 1

HCID 59747893Methyl 6-amino-5-iodo-2-methylnicotinate

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6228Dimethylformamide溶媒

反応条件

温度
50 °C

実験手順

Sodium periodate (4.05 g, 18.9 mmol) and iodine (9.62 g, 37.9 mmol) were added to a solution of methyl 6-amino-2-methylnicotinate (8.40 g, 50.5 mmol) in DMF (45 ml), and the mixture was then stirred at 50° C. for 1.5 hours. The reaction mixture was added to a cold solution of 250 ml of saturated sodium thiosulphate solution in 150 ml of water. The solid formed was filtered off with suction, washed with water and dried. This gave 13.4 mg (88.9% of theory) of methyl 6-amino-5-iodo-2-methylnicotinate. HPLC-MS: log P=1.55; mass (m/z): 293.0 (M+H)+; 1H-NMR (D6DMSO) 2.50 (s, 3H), 3.74 (s, 3H), 6.81 (br. s, 1H), 8.25 (s, 1H).

後処理

  1. customThe solid formed
  2. filtrationwas filtered off with suction
  3. washwashed with water
  4. customdried

出典と根拠

ORDレコード
ord-9a9b0fc43e0b408da246b9ba35be96df
出典データセット
uspto-grants-2016_05
特許番号
US09345247B2

反応ノート

読み込み中…