Hydrogen iodide → Methyl 4-amino-2-(trifluoromethyl)nicotinate

HRID 1170896ノート

反応式

HRID 1170896 の反応式
I.[N:2]([C:5]1[C:10]([C:11]([O:13][CH3:14])=[O:12])=[C:9]([C:15]([F:18])([F:17])[F:16])[N:8]=[CH:7][CH:6]=1)=[N+]=[N-]>ClCCl>[NH2:2][C:5]1[C:10]([C:11]([O:13][CH3:14])=[O:12])=[C:9]([C:15]([F:18])([F:16])[F:17])[N:8]=[CH:7][CH:6]=1

参加物

4

反応物 2

HCID 24841Hydrogen iodideHCID 59553876Methyl 4-azido-2-(trifluoromethyl)nicotinate

生成物 1

HCID 59553883Methyl 4-amino-2-(trifluoromethyl)nicotinate収率 51%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

Cold (0° C. ice bath) concentrated hydriodic acid (182 mL of a 57% aqueous solution) is added to methyl 4-azido-2-(trifluoromethyl)nicotinate (7.50 g, 30.5 mmol) in a flask. The mixture is stirred at 0° C. until TLC (ethyl acetate-hexanes, 75:25) shows complete consumption of starting material. The mixture is poured over an ice cold solution of potassium hydroxide (95 g of solid KOH dissolved in 300 mL of water). The mixture is extracted with diethyl ether. The ethereal layer is washed with water, dried over anhydrous magnesium sulfate, filtered and concentrated in vacuo to afford a yellow solid. The solid is dissolved in a minimal amount of dichloromethane and passed through a silica gel plug, eluting with ethyl acetate-hexanes (10:90). The eluant is concentrated to afford 3.42 g (51%) of methyl 4-amino-2-(trifluoromethyl)nicotinate as an off-white solid. 1HNMR (400 MHz, CD3OD), 8.11 (d, 1H), 6.93 (d, 1H), 3.878 (s, 3H). LC/MS (M+1)=221.2

後処理

  1. customconsumption of starting material
  2. additionThe mixture is poured over an ice cold solution of potassium hydroxide (95 g of solid KOH dissolved in 300 mL of water)
  3. extractionThe mixture is extracted with diethyl ether
  4. washThe ethereal layer is washed with water
  5. dry with materialdried over anhydrous magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customto afford a yellow solid
  9. washeluting with ethyl acetate-hexanes (10:90)
  10. concentrationThe eluant is concentrated

出典と根拠

ORDレコード
ord-a859611002f64a0da1ddd2bde5f4a84e
出典データセット
uspto-grants-2010_11
特許番号
US07829572B2

反応ノート

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