Hydrochloric Acid → 2-Amino-5-methoxy-4-(3-(pyrrolidin-1-yl)propoxy)benzamide hydrochloride

HRID 1386300ノート

反応式

HRID 1386300 の反応式
[ClH:1].[CH3:2][O:3][C:4]1[C:5]([O:16][CH2:17][CH2:18][CH2:19][N:20]2[CH2:24][CH2:23][CH2:22][CH2:21]2)=[CH:6][C:7]([N+:13]([O-])=O)=[C:8]([CH:12]=1)[C:9]([NH2:11])=[O:10]>CO.[Fe]>[ClH:1].[NH2:13][C:7]1[CH:6]=[C:5]([O:16][CH2:17][CH2:18][CH2:19][N:20]2[CH2:24][CH2:23][CH2:22][CH2:21]2)[C:4]([O:3][CH3:2])=[CH:12][C:8]=1[C:9]([NH2:11])=[O:10]

参加物

5

反応物 2

HCID 313Hydrochloric AcidHCID 218748225-Methoxy-2-nitro-4-(3-(pyrrolidin-1-yl)propoxy)benzamide

生成物 1

HCID 218748202-Amino-5-methoxy-4-(3-(pyrrolidin-1-yl)propoxy)benzamide hydrochloride収率 85%

試薬・触媒・溶媒 2

HCID 23925Iron触媒HCID 887Methanol溶媒

反応条件

温度
50 °C

実験手順

Concentrated hydrochloric acid (5 ml) was added to a suspension of 5-methoxy-2-nitro-4-(3-(pyrrolidin-1-yl)propoxy)benzamide (1.5 g, 4.64 mmol) in methanol (20 ml) and the mixture was heated at 50° C. to give a solution. Iron powder (1.3 g, 23.2 mmol) was added in portions and the reaction mixture was then heated at reflux for 1 hour. The mixture was allowed to cool, the insolubles were removed by filtration through diatomaceous earth and the volatiles were removed from the filtrate by evaporation. The residue was purified on a Diaion (trade mark of Mitsubishi) HP20SS resin column, eluting with water and then with dilute hydrochloric acid (pH2). The fractions containing product were concentrated by evaporation and the resulting precipitate was collected by filtration and dried under vacuum over phosphorus pentoxide to give 2-amino-5-methoxy-4-(3-(pyrrolidin-1-yl)propoxy)benzamide hydrochloride (1.44 g, 85%).

後処理

  1. customto give a solution
  2. temperaturethe reaction mixture was then heated
  3. temperatureat reflux for 1 hour
  4. temperatureto cool
  5. customthe insolubles were removed by filtration through diatomaceous earth
  6. customthe volatiles were removed from the filtrate by evaporation
  7. customThe residue was purified on a Diaion (trade mark of Mitsubishi) HP20SS resin column
  8. washeluting with water
  9. additionThe fractions containing product
  10. concentrationwere concentrated by evaporation
  11. filtrationthe resulting precipitate was collected by filtration
  12. dry with materialdried under vacuum over phosphorus pentoxide

出典と根拠

ORDレコード
ord-64b4e027b9d14f84b7f6da280335382d
出典データセット
uspto-grants-2001_07
特許番号
US06265411B1

反応ノート

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