6-Chloro-5-methylpyridin-3-amine → 6-Chloro-5-methylpyridin-3-ol

HRID 1160867

反応式

HRID 1160867 の反応式
[Cl:1][C:2]1[N:7]=[CH:6][C:5](N)=[CH:4][C:3]=1[CH3:9].N([O-])=[O:11].[Na+]>Cl.O>[Cl:1][C:2]1[N:7]=[CH:6][C:5]([OH:11])=[CH:4][C:3]=1[CH3:9]

参加物

5

反応物 2

HCID 122956076-Chloro-5-methylpyridin-3-amineHCID 23668193Sodium Nitrite

生成物 1

HCID 128520156-Chloro-5-methylpyridin-3-ol収率 33.6%

試薬・触媒・溶媒 2

HCID 313Hydrochloric Acid溶媒HCID 962Water溶媒

反応条件

温度
90 °C

実験手順

2-Chloro-3-methyl-5-nitro-pyridine (2 g, 11.6 mmol) and SnCl2.(H2O)2 (7.86 g, 34.8 mmol) are refluxed in MeOH overnight. After cooled down, the mixture is diluted with ethyl acetate, washed with water, brine, dried over MgSO4, concentrated and purified by column chromatography to afford 6-chloro-5-methyl-pyridin-3-ylamine (1.7 g). To the solution of 6-chloro-5-methyl-pyridin-3-ylamine (1.7 g, 11.6 mmol) in 1N HCl is added the solution of NaNO2 (960 mg, 13.92 mmol) in water (10 ml) slowly at 0° C. After the addition, the solution is stirred for 20 min and then heated to 90° C. for 30 min. The solution is cooled down, quenched with K2CO3, extracted with ether, dried over MgSO4, and purified by column chromatography to afford the titled compound (560 mg) as a yellow solid.

後処理

  1. additionAfter the addition
  2. temperatureThe solution is cooled down
  3. customquenched with K2CO3
  4. extractionextracted with ether
  5. dry with materialdried over MgSO4
  6. custompurified by column chromatography

出典と根拠

ORDレコード
ord-e2fa8982622b497c9f05cb38ac64b48d
出典データセット
uspto-grants-2010_10
特許番号
US07816557B2

関連ノート

読み込み中…