Ammonia → 3-Quinolinecarbonitrile, 2-amino-5,6,7,8-tetrahydro-

HRID 1199640ノート

反応式

HRID 1199640 の反応式
C(O[CH:4]=[C:5]([C:10]#[N:11])[CH:6](O)[C:7]#N)C.O1[CH2:16][CH2:15]CC1.[N:17]1([C:22]2CCCCC=2)CCCC1.[NH3:28].[CH2:29](O)[CH3:30]>CO.O>[NH2:17][C:22]1[C:30]([C:29]#[N:28])=[CH:4][C:5]2[CH2:6][CH2:7][CH2:16][CH2:15][C:10]=2[N:11]=1

参加物

8

反応物 5

HCID 222AmmoniaHCID 702EthanolHCID 8028Tetrahydrofuran2 回HCID 707681-Pyrrolidino-1-cyclohexeneHCID 539932842-(Ethoxymethylidene)-3-hydroxybutanedinitrile

生成物 1

HCID 112290713-Quinolinecarbonitrile, 2-amino-5,6,7,8-tetrahydro-収率 19%

試薬・触媒・溶媒 2

HCID 887Methanol溶媒HCID 962Water溶媒

反応条件

温度
0 °C

実験手順

To a mixture of 16 g (0.131 mol) of ethoxymethylenemalonitrile and 450 ml of tetrahydrofuran at -35° C. is added portionwise a mixture of 20 g (0.1322 mol) of 1-(pyrrolidino)-1-cyclohexene and 300 ml of tetrahydrofuran. After 2 hrs., the reaction mixture is allowed to warm to 0° C. for 30 min. To the reaction mixture at 0° C. is added 300 ml of a saturated solution of ammonia in methanol. The reaction mixture is stirred overnight at ambient temperature, diluted with water, and extracted with methylene chloride. The combined extracts are dried (Na2SO4) and concentrated in vacuo to give an oily solid. Trituration with ethanol affords 4.3 g (19%) of title compound. Recrystallization from ethanol provides an analytical sample: m.p. 192°-193° C.; IR (KBr) 3430, 3320, 3170, 2220, 1645, and 1600 cm-1 ; NMR (DMSO-d6)δ 7.55 (s, 1H), 6.45 (br-s, 2H, exchangeable), 2.7-2.35 (m, 4H, partially obscured by DMSO), and 1.85-1.55 (m, 4H).

後処理

  1. additionis added portionwise
  2. extractionextracted with methylene chloride
  3. dry with materialThe combined extracts are dried (Na2SO4)
  4. concentrationconcentrated in vacuo
  5. customto give an oily solid

出典と根拠

ORDレコード
ord-8068d8d80df948639bd82f967651ff7c
出典データセット
uspto-grants-1990_02
特許番号
US04902685

反応ノート

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