Ammonia → 2-Phenyl-2-[4-(1-methyl-1,2,3,4-tetrahydro-4-quinolyl)-phenoxy]-propionitrile

HRID 616196

반응식

HRID 616196 반응식
N.[C:2]1([CH:8]([O:11][C:12]2[CH:17]=[CH:16][C:15]([CH:18]3[C:27]4[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=4)[N:21]([CH3:28])[CH2:20][CH2:19]3)=[CH:14][CH:13]=2)[C:9]#[N:10])[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.S(OC)(O[CH3:33])(=O)=O>[N+]([O-])([O-])=O.[Fe+3].[N+]([O-])([O-])=O.[N+]([O-])([O-])=O>[C:2]1([C:8]([O:11][C:12]2[CH:17]=[CH:16][C:15]([CH:18]3[C:27]4[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=4)[N:21]([CH3:28])[CH2:20][CH2:19]3)=[CH:14][CH:13]=2)([CH3:33])[C:9]#[N:10])[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

참가 물질

5

반응물 3

HCID 222AmmoniaHCID 6497Dimethyl Sulfate2회HCID 203714312-Phenyl-2-[4-(1-methyl-1,2,3,4-tetrahydro-4-quinolyl)-phenoxy]-acetonitrile

생성물 1

HCID 203714302-Phenyl-2-[4-(1-methyl-1,2,3,4-tetrahydro-4-quinolyl)-phenoxy]-propionitrile

시약·촉매·용매 1

HCID 25251Ferric nitrate촉매

실험 절차

At -40°, 50 mg. of iron (III) nitrate and then, under agitation, 2.3 g. of Na are dissolved in 100 ml. of liquid ammonia. After two hours of agitation, 3.54 g. of 2-phenyl-2-[4-(1-methyl-1,2,3,4-tetrahydro-4-quinolyl)-phenoxy]-acetonitrile is added thereto, the mixture stirred for 30 minutes, and then 19.2 ml. of dimethyl sulfate is added dropwise within one hour. The mixture is further agitated overnight at -35° and then combined dropwise with another 10 ml. of dimethyl sulfate. After the ammonia has been evaporated, the residue is combined with water and extracted with ether. The crude 2-phenyl-2-[4-(1-methyl-1,2,3,4-tetrahydro-4-quinolyl)-phenoxy]-propionitrile obtained after the evaporation of the ether is refluxed for 40 hours with 3 g. of KOH in 30 ml. of ethanol and 3 ml. of water. The mixture is concentrated by evaporation, mixed with water, extracted with ether, hydrochloric acid is added to pH 5, and the acid Ih is thus produced.

후처리

  1. customAt -40°
  2. dissolutionof Na are dissolved in 100 ml
  3. stirringThe mixture is further agitated overnight at -35°
  4. customAfter the ammonia has been evaporated
  5. extractionextracted with ether

출처 및 근거

ORD 기록
ord-250b17d88f0f46d59e9a692e1469af56
출처 데이터셋
uspto-grants-1978_02
특허 번호
US04072754

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