N,N-Dimethylaniline → 2-Phenylindole

HRID 22933

反応式

HRID 22933 の反応式
CO[C:3]1[CH:8]=[CH:7][C:6]([NH2:9])=[CH:5][CH:4]=1.CN(C)C1C=CC=CC=1.CO[C:21]1[CH:26]=[CH:25][C:24]([C:27]([CH2:29]Br)=O)=[CH:23][CH:22]=1>CCOC(C)=O>[C:24]1([C:27]2[NH:9][C:6]3[C:7]([CH:29]=2)=[CH:8][CH:3]=[CH:4][CH:5]=3)[CH:25]=[CH:26][CH:21]=[CH:22][CH:23]=1

参加物

5

反応物 3

HCID 949N,N-DimethylanilineHCID 4965Bromomethyl 4-methoxyphenyl ketoneHCID 7732P-Anisidine

生成物 1

HCID 136982-Phenylindole

試薬・触媒・溶媒 1

HCID 8857Ethyl Acetate溶媒

実験手順

To a boiling mixture of in-anisidine (1.56 ml, 20.0 minol) and N,N-dimethylaniline (3.5 ml) was added 2-bromo-4-methoxyacetophenone (1.37 g in EtOAc, 6.00 mmol) slowly by syringe. After addition, the mixture was kept at 170° C. for 1 hour. The reaction mixture was cooled to room temperature and a dark colored solid was formed. EtOAc was added along with HCI (2 N). The aqueous layer was extracted with EtOAc several times. The combined organic layers were washed with brine, and dried over MgSO4. Solvent was removed under the reduced pressure to afford a dark brown colored solid. Purification by recrystallization in EtOH afforded indole 31 as a white crystallinc material.

後処理

  1. additionAfter addition
  2. customa dark colored solid was formed
  3. extractionThe aqueous layer was extracted with EtOAc several times
  4. washThe combined organic layers were washed with brine
  5. dry with materialdried over MgSO4
  6. customSolvent was removed under the reduced pressure
  7. customto afford a dark brown colored solid
  8. customPurification
  9. customby recrystallization in EtOH

出典と根拠

ORDレコード
ord-71e649dc94b4468a9952da8d86e5f34c
出典データセット
uspto-grants-2005_02
特許番号
US06849656B1

関連ノート

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