Ammonia → 3-Quinolinecarbonitrile, 2-amino-5,6,7,8-tetrahydro-
Reaction equation
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]=1Participants
Reactant 5
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 0 °C
Procedure
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).
Workup
- additionis added portionwise
- extractionextracted with methylene chloride
- dry with materialThe combined extracts are dried (Na2SO4)
- concentrationconcentrated in vacuo
- customto give an oily solid
Sources & evidence
- ORD record
- ord-8068d8d80df948639bd82f967651ff7c
- Source dataset
- uspto-grants-1990_02
- Patent number
- US04902685
Reaction notes
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