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

HRID 1390845

反応式

HRID 1390845 の反応式
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

参加物

5

反応物 2

HCID 20550574Trans-beta-dimethylamino-4-methyl-2-nitrostyreneHCID 178418361HCID 178418361、化合物

生成物 1

HCID 1379281H-Indole, 6-methyl-収率 83%

試薬・触媒・溶媒 2

HCID 23938Palladium触媒HCID 241Benzene溶媒

実験手順

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°.

後処理

  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

出典と根拠

ORDレコード
ord-b7bbbb3ec61d4003bab918a8c7e8175f
出典データセット
uspto-grants-1979_02
特許番号
US04140697

関連ノート

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