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

HRID 1857632ノート

反応式

HRID 1857632 の反応式
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]

参加物

4

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-4af0633ddbb6426a98e66bb63ee159cb
出典データセット
uspto-grants-2000_11
特許番号
US06147088

反応ノート

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