Ammonium Acetate → 1-[5-Chloro-8-(3-fluorophenyl)quinolin-7-yl]ethanamine

HRID 1192509노트

반응식

HRID 1192509 반응식
[Cl:1][C:2]1[CH:11]=[C:10]([C:12](=O)[CH3:13])[C:9]([C:15]2[CH:20]=[CH:19][CH:18]=[C:17]([F:21])[CH:16]=2)=[C:8]2[C:3]=1[CH:4]=[CH:5][CH:6]=[N:7]2.C([O-])(=O)C.[NH4+].C([BH3-])#[N:28].[Na+]>CO.C(#N)C>[Cl:1][C:2]1[CH:11]=[C:10]([CH:12]([NH2:28])[CH3:13])[C:9]([C:15]2[CH:20]=[CH:19][CH:18]=[C:17]([F:21])[CH:16]=2)=[C:8]2[C:3]=1[CH:4]=[CH:5][CH:6]=[N:7]2

참가 물질

6

반응물 3

HCID 517165Ammonium AcetateHCID 5003444Sodium cyanoborohydrideHCID 672483691-[5-Chloro-8-(3-fluorophenyl)quinolin-7-yl]ethanone

생성물 1

HCID 672492481-[5-Chloro-8-(3-fluorophenyl)quinolin-7-yl]ethanamine

시약·촉매·용매 2

HCID 887Methanol용매HCID 6342Acetonitrile용매

반응 조건

온도
65 °C

실험 절차

A mixture of 1-[5-chloro-8-(3-fluorophenyl)quinolin-7-yl]ethanone (76 mg, 0.25 mmol) and ammonium acetate (195 mg, 2.54 mmol) in methanol (1.4 mL) and acetonitrile (1.4 mL) was heated at 65° C. in a sealed tube for 30 minutes. After cooling, sodium cyanoborohydride (31.9 mg, 0.507 mmol) was added to the resultant mixture. The reaction was heated at 65° C. for another 4 hours, then cooled to room temperature, quenched with saturated sodium bicarbonate, and extracted with dichloromethane. The combined extracts were dried over magnesium sulfate and then evaporated to dryness. The residue was used directly in next step (52 mg, 68%). LCMS calculated for C17H15ClFN2(M+H)+: m/z=301.1; found: 301.0.

후처리

  1. temperatureAfter cooling
  2. temperatureThe reaction was heated at 65° C. for another 4 hours
  3. temperaturecooled to room temperature
  4. customquenched with saturated sodium bicarbonate
  5. extractionextracted with dichloromethane
  6. dry with materialThe combined extracts were dried over magnesium sulfate
  7. customevaporated to dryness

출처 및 근거

ORD 기록
ord-f21f6449ee384bdfb18f666e307d7bae
출처 데이터셋
uspto-grants-2014_03
특허 번호
US08680108B2

반응 노트

불러오는 중…