Cyclopentadiene → 7,9-dichloro-3a,4,5,9b-tetrahydro-3H-cyclopenta[c]quinoline-4-carboxylic acid

HRID 857431

反応式

HRID 857431 の反応式
[Cl:1][C:2]1[CH:3]=[C:4]([CH:6]=[C:7]([Cl:9])[CH:8]=1)[NH2:5].O.[C:11]([OH:15])(=[O:14])[CH:12]=O.[CH:16]1[CH2:20][CH:19]=[CH:18][CH:17]=1>C(#N)C>[Cl:1][C:2]1[CH:8]=[C:7]([Cl:9])[C:6]2[CH:18]3[CH:17]=[CH:16][CH2:20][CH:19]3[CH:12]([C:11]([OH:15])=[O:14])[NH:5][C:4]=2[CH:3]=1

参加物

5

反応物 3

HCID 7612CyclopentadieneHCID 122813,5-DichloroanilineHCID 15620607Glyoxylic acid, monohydrate

生成物 1

HCID 29147727,9-dichloro-3a,4,5,9b-tetrahydro-3H-cyclopenta[c]quinoline-4-carboxylic acid

試薬・触媒・溶媒 1

HCID 6342Acetonitrile溶媒

反応条件

温度
50 °C

実験手順

1.14 g of 3,5-dichloroaniline (10 mmol), 0.97 g of glyoxylic acid hydrate (15 mmol) and 1.40 g of cyclopentadiene (freshly distilled) (30 mmol) were dissolved in 20 ml of acetonitrile in a closable Teflon vessel and heated to 50° C. within one minute in a microwave oven with a power of 800 watts and kept at this temperature for five minutes with further microwave irradiation. The vessel was then placed in ice water, cautiously opened and evaporated in a rotary evaporator. The mass of crystals obtained was washed with hexane and dried. A colourless mass of crystals was obtained in a quantity of 1.95 g (98% of theoretical).

後処理

  1. customkept at this temperature for five minutes with further microwave irradiation
  2. customevaporated in a rotary evaporator
  3. customThe mass of crystals obtained
  4. washwas washed with hexane
  5. customdried
  6. customA colourless mass of crystals was obtained in a quantity of 1.95 g (98% of theoretical)

出典と根拠

ORDレコード
ord-660b88d475be4522bf20f672384a4b5a
出典データセット
uspto-grants-2006_12
特許番号
US07145011B2

関連ノート

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