Hydrochloric Acid → 1-[(Prop-2-en-1-yloxy)carbonyl]-1,2,3,6-tetrahydropyridine-4-carboxylic acid

HRID 1385890ノート

反応式

HRID 1385890 の反応式
Cl.[C:2]([OH:10])(=[O:9])[C:3]1[CH2:8][CH2:7][NH:6][CH2:5][CH:4]=1.C(=O)([O-])[O-].[Na+].[Na+].Cl[C:18]([O:20][CH2:21][CH:22]=[CH2:23])=[O:19].Cl>O.ClCCl>[CH2:21]([O:20][C:18]([N:6]1[CH2:7][CH2:8][C:3]([C:2]([OH:10])=[O:9])=[CH:4][CH2:5]1)=[O:19])[CH:22]=[CH2:23]

参加物

7

反応物 4

HCID 313Hydrochloric AcidHCID 10340Sodium CarbonateHCID 18052Allyl chloroformateHCID 155107Isoguvacine Hydrochloride

生成物 1

HCID 108567621-[(Prop-2-en-1-yloxy)carbonyl]-1,2,3,6-tetrahydropyridine-4-carboxylic acid収率 102.4%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6344Dichloromethane溶媒

実験手順

1,2,5,6-Tetrahydroisonicotinic acid hydrochloride (150 g, 0.92 mol) is added to an aqueous solution of sodium carbonate (194 g, 1.83 mol) in water (920 ml), and thereto is added dropwise 2-propenyl chloroformate (116 g, 0.96 mol) under ice-cooling over a period of one hour. After the addition, the mixture is further stirred under icecooling for five hours. Separately, conc. hydrochloric acid (191 g) and dichloromethane (1000 ml) are cooled, and thereto is added dropwise the above reaction mixture in portions. The mixture is separated, and the aqueous layer is extracted twice with dichloromethane. The organic layers are combined, washed with a saturated aqueous sodium chloride solution, dried over magnesium sulfate, and concentrated under reduced pressure to remove the solvent to give 1-(2-propenyloxycarbonyl)-1,2,5,6-tetrahydro-isonicotinic acid (198.9 g, quant.) as a white solid.

後処理

  1. temperaturecooling over a period of one hour
  2. additionAfter the addition
  3. additionis added dropwise the above reaction mixture in portions
  4. customThe mixture is separated
  5. extractionthe aqueous layer is extracted twice with dichloromethane
  6. washwashed with a saturated aqueous sodium chloride solution
  7. dry with materialdried over magnesium sulfate
  8. concentrationconcentrated under reduced pressure
  9. customto remove the solvent

出典と根拠

ORDレコード
ord-5011fed284c6434287798f43bdc64543
出典データセット
uspto-grants-2001_07
特許番号
US06265396B1

反応ノート

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