Hydrochloric Acid → Quinolinepropionic acid, 1,2,3,4-tetrahydro-

HRID 446039

反応式

HRID 446039 の反応式
[NH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH2:4][CH2:3][CH2:2]1.[C:11]([O:15]C)(=[O:14])[CH:12]=[CH2:13].[Li+].[OH-].Cl>C(O)(=O)C.CO>[N:1]1([CH2:13][CH2:12][C:11]([OH:15])=[O:14])[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH2:4][CH2:3][CH2:2]1

参加物

7

反応物 4

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 7294Methyl AcrylateHCID 694601,2,3,4-Tetrahydroquinoline

生成物 1

HCID 98707Quinolinepropionic acid, 1,2,3,4-tetrahydro-収率 63%

試薬・触媒・溶媒 2

HCID 176Acetic Acid溶媒HCID 887Methanol溶媒2 回

実験手順

A mixture of 1,2,3,4-tetrahydroquinoline (3.0 g, 22.5 mmol) and methyl acrylate (3.9 g, 45.0 mmol) in acetic acid (15 mL) was refluxed for 16 hours. Upon cooling, volatiles were removed in the rotary evaporator and the residue obtained was co-evaporated with methanol (3×20 mL) and then dissolved in methanol (15 mL). To this mixture an aqueous solution of LiOH (1.9 g, 45 mmol) was added and it was stirred at room temperature for 2 hours. Reaction mixture was acidified with conc. HCl to pH ˜3 and extracted with ethyl acetate. The organic layer was washed twice with water and brine, dried over MgSO4 and evaporated to dryness to yield 2.91 g of Compound 7 as a dark brown viscous liquid. This product was used without any further purification. The structure of Compound 7 is given below:

後処理

  1. temperaturewas refluxed for 16 hours
  2. temperatureUpon cooling
  3. customvolatiles were removed in the rotary evaporator
  4. customthe residue obtained
  5. customReaction mixture
  6. extractionextracted with ethyl acetate
  7. washThe organic layer was washed twice with water and brine
  8. dry with materialdried over MgSO4
  9. customevaporated to dryness

出典と根拠

ORDレコード
ord-6a1fab905f824568b9f23e84d7c8db81
出典データセット
uspto-grants-2013_07
特許番号
US08476443B2

関連ノート

読み込み中…