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Sulfuric Acid → 2-Chloro-3-methylpyridine-4-carboxylic acid

HRID 2208879
ノート
印刷プレビュー

反応式

HRID 2208879 の反応式
[Cl:1][C:2]1[C:7]([CH3:8])=[C:6]([C:9](N(C)C2C=CC=CC=2)=[O:10])[CH:5]=[CH:4][N:3]=1.[OH:19]S(O)(=O)=O.C([O-])([O-])=O.[Na+].[Na+]>O>[Cl:1][C:2]1[C:7]([CH3:8])=[C:6]([C:9]([OH:10])=[O:19])[CH:5]=[CH:4][N:3]=1
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

5

反応物 3

HCID 1118Sulfuric AcidHCID 10340Sodium CarbonateHCID 150757162-Chloro-N,3-dimethyl-N-phenylisonicotinamide

生成物 1

HCID 150757212-Chloro-3-methylpyridine-4-carboxylic acid収率 54%

試薬・触媒・溶媒 1

HCID 962Water溶媒

反応条件

温度
130 °C

実験手順

2-chloro-N,3-dimethyl-N-phenylpyridine-4-carboxamide (2.2 g, 8.5 mmol) was treated with a mixture of concentrated H2SO4 (23.2 ml) and water (16.8 ml) and then heated to 130° C. for 46 hours. After which time, the reaction mixture was allowed to reach room temperature and poured onto ice (200 ml) and stirred until the ice had melted. The mixture was made alkaline (pH 8) by the addition of solid Na2CO3 (50.3 g) portionwise. The suspension was filtered and the filtrate acidified to pH 3 by the addition of 6M HCl (aq) (˜1.5 ml). The resulting solid was collected by filtration, washed with water (20 ml) and dried in-vacuo at 40° C. for 10 hours to give the title compound (779 mg, 54%) as a pink solid. LC-MS 100%, m/z=171.9, 173.9; 1H NMR (500 MHz, MeOD) δ ppm 8.30 (d, J=4.89 Hz, 1H) 7.64 (d, J=5.04 Hz, 1H) 2.58 (s, 3H).

後処理

  1. customto reach room temperature
  2. additionpoured onto ice (200 ml)
  3. filtrationThe suspension was filtered
  4. additionthe filtrate acidified to pH 3 by the addition of 6M HCl (aq) (˜1.5 ml)
  5. filtrationThe resulting solid was collected by filtration
  6. washwashed with water (20 ml)
  7. customdried in-vacuo at 40° C. for 10 hours

出典と根拠

ORDレコード
ord-869f8efc23c44f1bb2383dedd51d2b3d
出典データセット
uspto-grants-2016_06
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US09376422B2

反応ノート

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