N,N-Dimethylaniline → 2-Phenylindole

HRID 22933

반응식

HRID 22933 반응식
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

참가 물질

5

반응물 3

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

생성물 1

HCID 136982-Phenylindole

시약·촉매·용매 1

HCID 8857Ethyl Acetate용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-71e649dc94b4468a9952da8d86e5f34c
출처 데이터셋
uspto-grants-2005_02
특허 번호
US06849656B1

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