alpha-Cyano-beta-(2-Nitro-4,5-Dimethoxyphenyl)Acrylamide → 2-Amino-6,7-dimethoxyquinoline-3-carboxamide

HRID 1283154

반응식

HRID 1283154 반응식
[C:1]([C:3](=[CH:7][C:8]1[CH:13]=[C:12]([O:14][CH3:15])[C:11]([O:16][CH3:17])=[CH:10][C:9]=1[N+:18]([O-])=O)[C:4]([NH2:6])=[O:5])#[N:2]>[Fe].C(O)(=O)C.CN(C)C=O>[CH3:15][O:14][C:12]1[CH:13]=[C:8]2[C:9](=[CH:10][C:11]=1[O:16][CH3:17])[N:18]=[C:1]([NH2:2])[C:3]([C:4]([NH2:6])=[O:5])=[CH:7]2

참가 물질

4

반응물 1

HCID 4145653alpha-Cyano-beta-(2-Nitro-4,5-Dimethoxyphenyl)Acrylamide

생성물 1

HCID 7815842-Amino-6,7-dimethoxyquinoline-3-carboxamide

시약·촉매·용매 2

HCID 23925Iron촉매2회HCID 21926011acetic acid N,N-dimethylformamide용매

반응 조건

온도
90 °C

실험 절차

Iron powder (65.2 g., 1.22 moles) is added over a period of one-half hour to a slurry of α-cyano-β-(2-nitro-4,5-dimethoxyphenyl)acrylamide (75.0g., 0.271 mole) in a 50% solution of acetic acid-N,N-dimethylformamide (750 ml.) at 75°C. When addition of the iron powder is complete, the mixture is heated to 90°C. for 4 hours and then filtered while hot. The filter cake is washed with hot acetic acid (150 ml.). The dark red filtrate is gradually added to IN hydrochloric acid (1500 ml.) and the pink precipitate recovered by filtration and recrystallized from an excess (10%) of aqueous sodium hydroxide. The solid is filtered, washed with cold isopropanol and dried to give the title product as yellow crystals. Yield = 57.1 g. (83.5%); mpp. 274°-275°C.

후처리

  1. filtrationfiltered while hot
  2. washThe filter cake is washed with hot acetic acid (150 ml.)
  3. additionThe dark red filtrate is gradually added to IN hydrochloric acid (1500 ml.)
  4. filtrationthe pink precipitate recovered by filtration
  5. customrecrystallized from an excess (10%) of aqueous sodium hydroxide
  6. filtrationThe solid is filtered
  7. washwashed with cold isopropanol
  8. customdried

출처 및 근거

ORD 기록
ord-5f23c007098249da9b1482b380cfbbf2
출처 데이터셋
uspto-grants-1976_08
특허 번호
US03974161

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