1,2-Dibromoethane → 9-(2-bromoethyl)-6-methyl-2,3,4,9-tetrahydro-1H-carbazol-1-one

HRID 1679821노트

반응식

HRID 1679821 반응식
[CH3:1][C:2]1[CH:3]=[C:4]2[C:12](=[CH:13][CH:14]=1)[NH:11][C:10]1[C:9](=[O:15])[CH2:8][CH2:7][CH2:6][C:5]2=1.[Br:16][CH2:17][CH2:18]Br.[OH-].[Na+].C1C=C2C3C=CN=CC=3NC2=CC=1>S([O-])(O)(=O)=O.C([N+](CCCC)(CCCC)CCCC)CCC.O>[CH3:1][C:2]1[CH:3]=[C:4]2[C:12](=[CH:13][CH:14]=1)[N:11]([CH2:18][CH2:17][Br:16])[C:10]1[C:9](=[O:15])[CH2:8][CH2:7][CH2:6][C:5]2=1

참가 물질

7

반응물 4

HCID 78391,2-DibromoethaneHCID 14798Sodium HydroxideHCID 64961Beta-CarbolineHCID 6079846-methyl-2,3,4,9-tetrahydro-1H-carbazol-1-one

생성물 1

HCID 8383119-(2-bromoethyl)-6-methyl-2,3,4,9-tetrahydro-1H-carbazol-1-one

시약·촉매·용매 2

HCID 94433Tetrabutylammonium hydrogen sulfate촉매2회HCID 962Water용매

실험 절차

199 g. (1 mole) of 6-methyl-1,2,3,4-tetrahydrocarbazol-1-one (m.p.: 199° C., as given in literature: 194°-195° C., 195°-196° C., 195° C., cf. Bloink and Pausacker loc. cit. page 1330), 1520 g. (8.1 moles), 1.2-dibromoethane and 1000 ml. (7.5 moles) of aqueous sodium hydroxide solution (30% strength) are taken initially and admixed, while stirring at room temperature, with 4.25 g. (12.5 m mole) of tetrabutylammoniumhydrogensulfate dissolved in 25 ml of water. With a slight temperature rise, the reaction sets in and while continuously stirring, comes to an end after some seven hours' time. For working up, the aqueous alkaline layer is separated, the organic layer washed with water and the excess dibromoethane distilled off in vacuo. The residue is recrystallized from 200 ml. of ethanol. Obtained are 281 g.=92% of the theoretical of 6-methyl-9-(2-ethylbromide)-1,2,3,4-tetrahydrocarbazol-1-one melting at 103° C. The amount of the tetrabutylammoniumhydrogensulfate used as catalyst can be reduced to 5 m moles per 1 mole of the carbazoline employed. During the procedure the reaction takes twice as long.

후처리

  1. stirringwhile continuously stirring
  2. customthe aqueous alkaline layer is separated
  3. washthe organic layer washed with water
  4. distillationthe excess dibromoethane distilled off in vacuo
  5. customThe residue is recrystallized from 200 ml
  6. customObtained

출처 및 근거

ORD 기록
ord-679021c695904895a241bcbe6469e909
출처 데이터셋
uspto-grants-1981_06
특허 번호
US04271073

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