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Acetic Acid → [3-[(Dimethylamino)methyl]-1H-indol-7-yl]phenylmethanone

HRID 1722465
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HRID 1722465 반응식
[CH3:1][NH:2][CH3:3].[C:4](O)(=O)C.C=O.[C:10]([C:18]1[CH:19]=[CH:20][CH:21]=[C:22]2[C:26]=1[NH:25][CH:24]=[CH:23]2)(=[O:17])[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1>C(O)C>[CH3:1][N:2]([CH2:4][C:23]1[C:22]2[C:26](=[C:18]([C:10]([C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=3)=[O:17])[CH:19]=[CH:20][CH:21]=2)[NH:25][CH:24]=1)[CH3:3]
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

6

반응물 4

HCID 176Acetic Acid2회HCID 674DimethylamineHCID 712FormaldehydeHCID 10878711(1H-Indol-7-yl)(phenyl)methanone

생성물 1

HCID 14279603[3-[(Dimethylamino)methyl]-1H-indol-7-yl]phenylmethanone

시약·촉매·용매 1

HCID 702Ethanol용매

실험 절차

An 18.0 g (0.16 mole) portion of 40% aqueous dimethylamine was cooled to 5° C. and 24 g (0.4 mole) of glacial acetic acid was added. To this mixture, held at 5° C., was added 12.2 g (0.15 mole) of 37% formalin. This aqueous mixture was added to a mixture of 33.1 g (0.15 mole) of 7-benzoyl-1H-indole and 20 ml of acetic acid. After 100 ml of absolute ethanol was added to the mixture, it was warmed on a steam bath for 1/2 hr. Isolation of the product was accomplished by concentrating the mixture under reduced pressure, partitioning between dilute sodium hydroxide and methylene chloride and concentrating the organic solution. The residue was recrystallized from isopropyl alcohol to give 29 g (70 %) of light yellow crystals, m.p. 111.0°-113.5° C.

후처리

  1. customheld at 5° C.
  2. temperaturewas warmed on a steam bath for 1/2 hr
  3. concentrationby concentrating the mixture under reduced pressure
  4. custompartitioning between dilute sodium hydroxide and methylene chloride
  5. concentrationconcentrating the organic solution
  6. customThe residue was recrystallized from isopropyl alcohol
  7. customto give 29 g (70 %) of light yellow crystals, m.p. 111.0°-113.5° C.

출처 및 근거

ORD 기록
ord-2bd9980935304e6ba236908cc3ea9d40
출처 데이터셋
uspto-grants-1989_08
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US04855447

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