Trans-beta-dimethylamino-4-methyl-2-nitrostyrene → 1H-Indole, 6-methyl-

HRID 1390845

반응식

HRID 1390845 반응식
CN(C)/[CH:3]=[CH:4]/[C:5]1[CH:10]=[CH:9][C:8]([CH3:11])=[CH:7][C:6]=1[N+:12]([O-])=O.[H][H]>C1C=CC=CC=1.[Pd]>[CH3:11][C:8]1[CH:7]=[C:6]2[C:5]([CH:4]=[CH:3][NH:12]2)=[CH:10][CH:9]=1

참가 물질

5

반응물 2

HCID 20550574Trans-beta-dimethylamino-4-methyl-2-nitrostyreneHCID 178418361HCID 178418361, 화합물

생성물 1

HCID 1379281H-Indole, 6-methyl-수율 83%

시약·촉매·용매 2

HCID 23938Palladium촉매HCID 241Benzene용매

실험 절차

A glass-lined rocking autoclave was charged with a solution of 300 g (1.45 moles) of trans-β-dimethylamino-4-methyl-2-nitrostyrene in 3 l of benzene and 15 g of 5% palladium on carbon. Th autoclave was pressurized with 20 psi of hydrogen and rocked for 5 hours. The mixture was filtered through a bed of Celite, which was washed thoroughly with benzene. The filtrate was concentrated to half its volume and washed with 1 l of 0.25N hydrochloric acid, 500 ml of saturated sodium bicarbonate and 500 ml of brine. The aqueous phases were backwashed with 500 ml of benzene and the combined organic phases were dried over sodium sulfate and concentrated. The residual dark brown oil was distilled at vacuo to afford 157.9 g (83%) of product as a light yellow oil, b.p. 80-85°/0.05 mmHg, which solidified after seeding to a light yellow solid. m.p. 29-30.5°.

후처리

  1. filtrationThe mixture was filtered through a bed of Celite, which
  2. washwas washed thoroughly with benzene
  3. concentrationThe filtrate was concentrated to half its volume
  4. washwashed with 1 l of 0.25N hydrochloric acid, 500 ml of saturated sodium bicarbonate and 500 ml of brine
  5. dry with materialthe combined organic phases were dried over sodium sulfate
  6. concentrationconcentrated
  7. distillationThe residual dark brown oil was distilled at vacuo

출처 및 근거

ORD 기록
ord-b7bbbb3ec61d4003bab918a8c7e8175f
출처 데이터셋
uspto-grants-1979_02
특허 번호
US04140697

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