Benzonitrile, m-chloro- → 7-bromo-3-(3-chlorophenyl)isoquinolin-1(2H)-one

HRID 77388

반응식

HRID 77388 반응식
C([N-]C(C)C)(C)C.[Li+].[Br:9][C:10]1[CH:11]=[CH:12][C:13]([CH3:20])=[C:14]([CH:19]=1)[C:15]([NH:17][CH3:18])=[O:16].[Cl:21][C:22]1[CH:23]=[C:24]([CH:27]=[CH:28][CH:29]=1)C#N.[NH4+].[Cl-]>O1CCCC1>[Br:9][C:10]1[CH:19]=[C:14]2[C:13]([CH:20]=[C:18]([C:28]3[CH:27]=[CH:24][CH:23]=[C:22]([Cl:21])[CH:29]=3)[NH:17][C:15]2=[O:16])=[CH:12][CH:11]=1

참가 물질

6

반응물 4

HCID 13015Benzonitrile, m-chloro-HCID 25517Ammonium ChlorideHCID 2724682Lithium diisopropylamideHCID 231569135-bromo-N,2-dimethylbenzamide2회

생성물 1

HCID 699288937-bromo-3-(3-chlorophenyl)isoquinolin-1(2H)-one수율 20.5%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매3회

반응 조건

온도
-78 °C

실험 절차

To a solution of 2M lithium diisopropylamide (19.73 mL, 39.5 mmol) in tetrahydrofuran (30 mL) at −78° C. was added dropwise a solution of 5-bromo-N,2-dimethylbenzamide (Intermediate 22A) (3.0 g, 13.15 mmol) in THF (14 mL) followed by a solution of 3-chlorobenzonitrile (1.809 g, 13.15 mmol) in THF (14 mL) and the mixture was stirred at −78° C. for 2.5 hours. Reaction allowed to warm to room temperature and saturated NH4Cl (aq) was added. The THF was removed under reduced pressure and the resulting mixture extracted into ethyl acetate and washed with brine (precipitate was observed in both layers). Organics were evaporated to dryness, washed with methanol and dried in a vacuum oven to afford 7-bromo-3-(3-chlorophenyl)isoquinolin-1(2H)-one (0.9 g, 2.69 mmol).

후처리

  1. customReaction
  2. temperatureto warm to room temperature
  3. customThe THF was removed under reduced pressure
  4. extractionthe resulting mixture extracted into ethyl acetate
  5. washwashed with brine (precipitate
  6. customOrganics were evaporated to dryness
  7. washwashed with methanol
  8. customdried in a vacuum oven

출처 및 근거

ORD 기록
ord-d4f48ef7718646d88df61971e710820c
출처 데이터셋
uspto-grants-2014_09
특허 번호
US08841289B2

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