Sodium Carbonate → 6,7-Diethoxy-4-(indan-5-ylamino)-quinoline-3-carbonitrile

HRID 1595762

반응식

HRID 1595762 반응식
Cl[C:2]1[C:11]2[C:6](=[CH:7][C:8]([O:15][CH2:16][CH3:17])=[C:9]([O:12][CH2:13][CH3:14])[CH:10]=2)[N:5]=[CH:4][C:3]=1[C:18]#[N:19].[NH2:20][C:21]1[CH:22]=[C:23]2[C:27](=[CH:28][CH:29]=1)[CH2:26][CH2:25][CH2:24]2.C(=O)([O-])[O-].[Na+].[Na+]>COCCO>[CH2:13]([O:12][C:9]1[CH:10]=[C:11]2[C:6](=[CH:7][C:8]=1[O:15][CH2:16][CH3:17])[N:5]=[CH:4][C:3]([C:18]#[N:19])=[C:2]2[NH:20][C:21]1[CH:22]=[C:23]2[C:27](=[CH:28][CH:29]=1)[CH2:26][CH2:25][CH2:24]2)[CH3:14]

참가 물질

5

반응물 3

HCID 10340Sodium CarbonateHCID 90496Indan-5-amineHCID 107788724-Chloro-6,7-diethoxyquinoline-3-carbonitrile

생성물 1

HCID 99695786,7-Diethoxy-4-(indan-5-ylamino)-quinoline-3-carbonitrile수율 80.6%

시약·촉매·용매 1

HCID 80192-Methoxyethanol용매

반응 조건

온도
100 °C

실험 절차

A solution of 400 mg (1.44 mM) of 4-chloro-6,7-diethoxy-quinoline-3-carbonitrile and 205 mg (1.54 mM) of 5-Aminoindan in 12 ml of 2-methoxyethanol was refluxed for 3 hours. To the warm solution was added 1 ml of 1M sodium carbonate and the sample was heated for 5 minutes at 100° C., then poured into 300 ml of ice water. The solid was collected, washed with water followed by ether and dried under vacuum at 80° C. The brown solid was dissolved digested in 200 ml of ethanol and the volume was reduced to 100 ml. The solid was isolated from the warm solution and washed with ethanol followed by ether and dried under vacuum at 80° C. to yield 435 mg of 6,7-Diethoxy-4-(indan-5-ylamino)-quinoline-3-carbonitrile as a brown solid: mass spectrum (electrospray, m/e): M+H 374.0, mp=85-88° C.

후처리

  1. customThe solid was collected
  2. washwashed with water
  3. customdried under vacuum at 80° C
  4. dissolutionThe brown solid was dissolved
  5. customThe solid was isolated from the warm solution
  6. washwashed with ethanol
  7. customdried under vacuum at 80° C.

출처 및 근거

ORD 기록
ord-4a07fb608e974b888aff2936eb62d2a1
출처 데이터셋
uspto-grants-2001_09
특허 번호
US06288082B1

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