Aniline → Ethyl 8-methoxy-4-(phenylamino)quinoline-3-carboxylate

HRID 66775

반응식

HRID 66775 반응식
Cl[C:2]1[C:11]2[C:6](=[C:7]([O:12][CH3:13])[CH:8]=[CH:9][CH:10]=2)[N:5]=[CH:4][C:3]=1[C:14]([O:16][CH2:17][CH3:18])=[O:15].[NH2:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1>O1CCCC1>[C:20]1([NH:19][C:2]2[C:11]3[C:6](=[C:7]([O:12][CH3:13])[CH:8]=[CH:9][CH:10]=3)[N:5]=[CH:4][C:3]=2[C:14]([O:16][CH2:17][CH3:18])=[O:15])[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1

참가 물질

4

반응물 2

HCID 6115AnilineHCID 3045573-Quinolinecarboxylic acid, 4-chloro-8-methoxy-, ethyl ester

생성물 1

HCID 1507948Ethyl 8-methoxy-4-(phenylamino)quinoline-3-carboxylate수율 95.1%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

실험 절차

To a solution of 6.0 g (22.5 mmoles) of ethyl 4-chloro-8-methoxy-3-quinolinecarboxylate in 80 ml of tetrahydrofuran was added 2.3 g (24.8 mmoles) of aniline in 60 ml of tetrahydrofuran. The solution was briefly warmed and after standing for 10 minutes, a yellow solid began to precipitate. The mixture was kept at room temperature for 18 hours. The solvent was rotary evaporated. The residue dissolved in 200 ml of methanol and the pH made slightly basic (pH 8) with sodium bicarbonate. Water (700 ml) was added and an oil formed which solidified and after standing, additional solid crystallized. The solid was filtered and air-dried to give 6.9 g (95%) of crude material. The solid was dissolved in 300 ml of hot isooctane and the solution was charcoaled and filtered. The volume of the filtrate was reduced to 150 ml. Upon cooling, pale yellow needles separated; 6.5 g (89%); m.p. 120°-121° C.

후처리

  1. temperatureThe solution was briefly warmed
  2. customto precipitate
  3. waitThe mixture was kept at room temperature for 18 hours
  4. dissolutionThe residue dissolved in 200 ml of methanol
  5. additionWater (700 ml) was added
  6. customan oil formed which
  7. customadditional solid crystallized
  8. filtrationThe solid was filtered
  9. customair-dried

출처 및 근거

ORD 기록
ord-30923a12ae1f4c92948fb4334f7c924e
출처 데이터셋
uspto-grants-1982_08
특허 번호
US04343804

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