Hydrochloric Acid → 5-Cyanotryptamine

HRID 1666798ノート

反応式

HRID 1666798 の反応式
Cl.[N+:2]([CH2:5][CH2:6][C:7]1[C:15]2[C:10](=[CH:11][CH:12]=[C:13]([C:16]#[N:17])[CH:14]=2)[NH:9][CH:8]=1)([O-])=O.[OH-].[Na+]>CO.[Zn]>[C:16]([C:13]1[CH:14]=[C:15]2[C:10]([NH:9][CH:8]=[C:7]2[CH2:6][CH2:5][NH2:2])=[CH:11][CH:12]=1)#[N:17]

参加物

6

反応物 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 21071455HCID 21071455、化合物

生成物 1

HCID 589265-Cyanotryptamine

試薬・触媒・溶媒 2

HCID 23994Zinc触媒HCID 887Methanol溶媒

実験手順

Add zinc powder (16.22 g, 248.1 mmol) in four portions to 2N HCl (300.0 ml). Add dropwise 3-(2-nitroethyl)-5-cyano-1H-indole (2.25 g, 10.5 mmol) as a solution in methanol (300.0 ml). Heat to reflux. After 2.5 hours, cool to ambient temperature and adjust the pH to 11 using 5N NaOH, filter through Celite, wash with water, then extract the filtrate with dichloromethane. Combine the organic extracts, wash with brine, dry (Na2SO4), then evaporated to give the title compound: mp 102-105° C., MS (ACPI): m/e 186.1 (M+1). Analysis for C11H11N3: Calcd: C, 71.33; H, 5.99; N, 22.69. found: C, 71.03; H, 5.91; N, 22.64.

後処理

  1. temperatureHeat to reflux
  2. filtrationfilter through Celite
  3. washwash with water
  4. extractionextract the filtrate with dichloromethane
  5. washwash with brine
  6. dry with materialdry (Na2SO4)
  7. customevaporated

出典と根拠

ORDレコード
ord-5c88f5d917d64303bcf42cee0e337f7b
出典データセット
uspto-grants-2011_10
特許番号
US08044090B2

反応ノート

読み込み中…