Hydrochloric Acid → 6-(Cyclohexyloxy)-3-pyridinecarboxylic acid

HRID 341537ノート

反応式

HRID 341537 の反応式
Cl[C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[CH:4][N:3]=1.[OH-].[K+].[CH:13]1([OH:19])[CH2:18][CH2:17][CH2:16][CH2:15][CH2:14]1.Cl>CS(C)=O>[CH:13]1([O:19][C:2]2[N:3]=[CH:4][C:5]([C:6]([OH:8])=[O:7])=[CH:9][CH:10]=2)[CH2:18][CH2:17][CH2:16][CH2:15][CH2:14]1

参加物

6

反応物 4

HCID 313Hydrochloric AcidHCID 7966CyclohexanolHCID 14797Potassium HydroxideHCID 792226-Chloronicotinic acid

生成物 1

HCID 167944166-(Cyclohexyloxy)-3-pyridinecarboxylic acid収率 55.5%

試薬・触媒・溶媒 1

HCID 679Dimethyl Sulfoxide溶媒

実験手順

6-Chloronicotinic acid (0.500 g, 3.17 mmol), powdered potassium hydroxide (0.712 g, 12.69 mmol) and cyclohexanol (0.636 g, 6.35 mmol) were combined in DMSO (12 mL) and heated in a sealed tube to 100 C for 18 h and then to 120 C for 21 h. The mixture was acidified to pH 1 by adding 2M hydrochloric acid. The mixture was then left to stand at room temperature overnight and the resultant precipitate filtered off, washed with water and dried under vacuum to afford the title compound as a cream solid (0.389 g, 55%). 1H NMR (500 MHZ, MeOH-d4) δ ppm 8.76 (1H, d), 8.19 (1H, dd), 6.79 (1H, d), 5.11 (1H, m), 2.03 (2H, m), 1.83 (2H, m), 1.64 (1H, m), 1.56 (2H, m), 1.47 (2H, m) and 1.38 (1H, m).

後処理

  1. temperatureheated in a sealed tube to 100 C for 18 h
  2. waitThe mixture was then left
  3. waitto stand at room temperature overnight
  4. filtrationthe resultant precipitate filtered off
  5. washwashed with water
  6. customdried under vacuum

出典と根拠

ORDレコード
ord-3cf3347008c543fe83d23733599b4dc3
出典データセット
uspto-grants-2014_11
特許番号
US08895733B2

反応ノート

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