Sodium bis(trimethylsilyl)amide → 6-allyl-7-chloro-3-(3,5-dimethylphenyl)-4-hydroxy-1H-quinolin-2-one

HRID 1857632노트

반응식

HRID 1857632 반응식
C[O:2][C:3](=O)[C:4]1[CH:9]=[C:8]([CH2:10][CH:11]=[CH2:12])[C:7]([Cl:13])=[CH:6][C:5]=1[NH:14][C:15](=[O:25])[CH2:16][C:17]1[CH:22]=[C:21]([CH3:23])[CH:20]=[C:19]([CH3:24])[CH:18]=1.C[Si]([N-][Si](C)(C)C)(C)C.[Na+]>O1CCCC1>[CH2:10]([C:8]1[CH:9]=[C:4]2[C:5](=[CH:6][C:7]=1[Cl:13])[NH:14][C:15](=[O:25])[C:16]([C:17]1[CH:18]=[C:19]([CH3:24])[CH:20]=[C:21]([CH3:23])[CH:22]=1)=[C:3]2[OH:2])[CH:11]=[CH2:12]

참가 물질

4

반응물 2

HCID 2724254Sodium bis(trimethylsilyl)amideHCID 542443075-Allyl-4-chloro-2-[2-(3,5-dimethylphenyl)-acetylamino]-benzoic acid methyl ester

생성물 1

HCID 547112376-allyl-7-chloro-3-(3,5-dimethylphenyl)-4-hydroxy-1H-quinolin-2-one수율 75%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

To a solution of 5-allyl-4-chloro-2-[2-(3,5-dimethylphenyl)-acetylamino]-benzoic acid methyl ester (1.4 g in 40 mL dry tetrahydrofuran) at 0° C. was added dropwise a solution of sodium bis(trimethylsilyl)amide (9.8 mL of a 1.0M solution in tetrahydrofuran) and the mixture warmed to room temperature. After 4 hours, the reaction was cooled to 0° C. and quenched by the addition of of 200 mL iced 6N hydrochloric acid. The slurry was stirred for 15 minutes then filtered and washed sequentially with ice water (500 mL), cold hexane (200 mL) and cold toluene (100 mL). The residue was dried in vacuo to give the title compound (960 mg).

후처리

  1. temperaturethe reaction was cooled to 0° C.
  2. customquenched by the addition of of 200 mL iced 6N hydrochloric acid
  3. filtrationthen filtered
  4. washwashed sequentially with ice water (500 mL), cold hexane (200 mL) and cold toluene (100 mL)
  5. customThe residue was dried in vacuo

출처 및 근거

ORD 기록
ord-4af0633ddbb6426a98e66bb63ee159cb
출처 데이터셋
uspto-grants-2000_11
특허 번호
US06147088

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