Sodium Hydroxide → 5-Bromo-3-iodopyridin-2-ol

HRID 229639

반응식

HRID 229639 반응식
N[C:2]1[C:7]([I:8])=[CH:6][C:5]([Br:9])=[CH:4][N:3]=1.N([O-])=[O:11].[Na+].[OH-].[Na+]>S(=O)(=O)(O)O>[Br:9][C:5]1[CH:6]=[C:7]([I:8])[C:2](=[O:11])[NH:3][CH:4]=1

참가 물질

5

반응물 3

HCID 14798Sodium HydroxideHCID 15165082-Amino-5-bromo-3-iodopyridineHCID 23668193Sodium Nitrite

생성물 1

HCID 120277875-Bromo-3-iodopyridin-2-ol

시약·촉매·용매 1

HCID 1118Sulfuric Acid용매

실험 절차

2-Amino-5-bromopyridine (CAS No. 1072-97-5) (300 g) was dissolved in a mixed solvent consisting of 1000 ml of acetic acid and 200 ml of water, 30 ml of concentrated sulfuric acid were gradually dropped thereinto under stirring. Then, 79.1 g of periodic acid hydrate and 176 g of iodine were added thereto, followed by stirring at 80° C. for 4 hours. To the reaction mixture were added periodic acid hydrate (40 g) and iodine (22 g), followed by further stirring at 80° C. for 2 hours. After cooling to room temperature, the reaction mixture was poured onto ice (3000 ml) and neutralized to pH 7.0 with 5N aqueous sodium hydroxide. The resulting crystals were collected by filtration, dissolved in a mixed solvent of ethyl acetate/diethyl ether, successively washed with aqueous sodium thiosulfate, water, 1N aqueous sodium hydroxide and brine, and dried over anhydrous magnesium sulfate. Then, the solvent was evaporated, to give 392 g of 2-amino-5-bromo-3-iodopyridine (yield: 76%). 2-Amino-5-bromo-3-iodopyridine (100 g) was gradually added to 300 ml of concentrated sulfuric acid under ice-cooling. After the reaction mixture was stirred at room temperature for 2 hours, it was ice-cooled again. 35 g of sodium nitrite were gradually added thereto, followed by stirring at room temperature for 3 days and nights. The reaction solution was poured onto ice (3000 ml) and neutralized to pH 4.0 with sodium hydroxide. The resulting crystals were collected by filtration, washed with water and warm air-dried at 60° C. for one day and night, to give 102 g (quantitative) of the title compound.

후처리

  1. temperaturecooling
  2. temperaturecooled again
  3. stirringby stirring at room temperature for 3 days and nights
  4. additionThe reaction solution was poured onto ice (3000 ml)
  5. filtrationThe resulting crystals were collected by filtration
  6. washwashed with water
  7. temperaturewarm
  8. customair-dried at 60° C. for one day and night

출처 및 근거

ORD 기록
ord-3a6965d51fa34b7ab55fbf60745e3aa0
출처 데이터셋
uspto-grants-2009_07
특허 번호
US07563811B2

연결된 노트

불러오는 중…