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

HRID 77388

反応式

HRID 77388 の反応式
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

参加物

6

反応物 4

HCID 13015Benzonitrile, m-chloro-HCID 25517Ammonium ChlorideHCID 2724682Lithium diisopropylamideHCID 231569135-bromo-N,2-dimethylbenzamide2 回

生成物 1

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

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒3 回

反応条件

温度
-78 °C

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-d4f48ef7718646d88df61971e710820c
出典データセット
uspto-grants-2014_09
特許番号
US08841289B2

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