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

HRID 1199640노트

반응식

HRID 1199640 반응식
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

참가 물질

8

반응물 5

HCID 222AmmoniaHCID 702EthanolHCID 8028Tetrahydrofuran2회HCID 707681-Pyrrolidino-1-cyclohexeneHCID 539932842-(Ethoxymethylidene)-3-hydroxybutanedinitrile

생성물 1

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

시약·촉매·용매 2

HCID 887Methanol용매HCID 962Water용매

반응 조건

온도
0 °C

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-8068d8d80df948639bd82f967651ff7c
출처 데이터셋
uspto-grants-1990_02
특허 번호
US04902685

반응 노트

불러오는 중…