Sodium bis(trimethylsilyl)amide → 7-chloro-4-hydroxy-6-nitro-3-(thiophen-2-yl)quinolin-2(1H)-one

HRID 1275590노트

반응식

HRID 1275590 반응식
CO[C:3](=[O:23])[C:4]1[CH:9]=[C:8]([N+:10]([O-:12])=[O:11])[C:7]([Cl:13])=[CH:6][C:5]=1[NH:14][C:15](=[O:22])[CH2:16][C:17]1[S:18][CH:19]=[CH:20][CH:21]=1.C[Si]([N-][Si](C)(C)C)(C)C.[Na+]>O1CCCC1>[Cl:13][C:7]1[CH:6]=[C:5]2[C:4]([C:3]([OH:23])=[C:16]([C:17]3[S:18][CH:19]=[CH:20][CH:21]=3)[C:15](=[O:22])[NH:14]2)=[CH:9][C:8]=1[N+:10]([O-:12])=[O:11]

참가 물질

4

반응물 2

HCID 2724254Sodium bis(trimethylsilyl)amideHCID 54055967Methyl 4-chloro-5-nitro-2-(2-(thiophen-2-yl)acetamido)benzoate

생성물 1

HCID 547119717-chloro-4-hydroxy-6-nitro-3-(thiophen-2-yl)quinolin-2(1H)-one수율 66.8%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

To a solution of 4-chloro-5-nitro-2-(2-thiophen-2-yl-acetylamino)-benzoic acid methyl ester (130 mg in 4.0 mL dry tetrahydrofuran) at 0° C. was added dropwise a solution of sodium bis(trimethylsilyl)amide (0.92 mL of a 1.0M solution in tetrahydrofuran) and the mixture warmed to room temperature. After 3 hours, the reaction was quenched by the addition of 6N hydrochloric acid. The slurry was stirred for 10 minutes then filtered and washed with ice cold acetonitrile. The residue was dried in vacuo to give the title compound (79 mg).

후처리

  1. customthe reaction was quenched by the addition of 6N hydrochloric acid
  2. filtrationthen filtered
  3. washwashed with ice cold acetonitrile
  4. customThe residue was dried in vacuo

출처 및 근거

ORD 기록
ord-6df337286c3d400c9d166282ebbb73e8
출처 데이터셋
uspto-grants-2000_12
특허 번호
US06162813

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