Ammonium Chloride → 4-(4-Amino-thiophen-2-ylmethyl)-2H-phthalazin-1-one

HRID 600270노트

반응식

HRID 600270 반응식
[N+:1]([C:4]1[CH:5]=[C:6]([CH2:9][C:10]2[C:19]3[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=3)[C:13](=[O:20])[NH:12][N:11]=2)[S:7][CH:8]=1)([O-])=O.[Cl-].[NH4+]>C(O)C.O.[Fe]>[NH2:1][C:4]1[CH:5]=[C:6]([CH2:9][C:10]2[C:19]3[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=3)[C:13](=[O:20])[NH:12][N:11]=2)[S:7][CH:8]=1

참가 물질

6

반응물 2

HCID 25517Ammonium ChlorideHCID 598565794-(4-Nitro-thiophen-2-ylmethyl)-2H-phthalazin-1-one

생성물 1

HCID 598565584-(4-Amino-thiophen-2-ylmethyl)-2H-phthalazin-1-one

시약·촉매·용매 3

HCID 23925Iron촉매HCID 702Ethanol용매HCID 962Water용매

반응 조건

온도
80 °C

실험 절차

To a suspension of 4-(4-nitro-thiophen-2-ylmethyl)-2H-phthalazin-1-one (27) (0.90 g, 5.71 mmol) in ethanol (25 mL) under a nitrogen blanket was added dropwise a solution of ammonium chloride (0.31 g, 5.7 mmol) in water 18 mL). After stirring the resultant solution for 5 minutes, iron powder (0.64 g, 11.5 mmol) was added in one portion. The yellow mixture was stirred at 80° C. for 3 hours. The reaction mixture was filtered hot through celite which was washed with ethyl acetate (80 mL). The concentrated in vacuo and then diluted with ethyl acetate (20 mL) washed with brine (20 mL), dried over magnesium, sulphate and dried in vacuo to afford the title cpd as a bright yellow powder. Single peak in LC-MS analysis, (0.68 g, 84% purity and required no further purification; m/z (LC-MS, ESP), RT=2.94 (M+H) 258.

후처리

  1. filtrationThe reaction mixture was filtered hot through celite which
  2. washwas washed with ethyl acetate (80 mL)
  3. concentrationThe concentrated in vacuo
  4. additiondiluted with ethyl acetate (20 mL)
  5. washwashed with brine (20 mL)
  6. dry with materialdried over magnesium, sulphate
  7. customdried in vacuo
  8. customto afford the title cpd as a bright yellow powder
  9. customno further purification
  10. customm/z (LC-MS, ESP), RT=2.94 (M+H) 258

출처 및 근거

ORD 기록
ord-84f76ef90b654fa28d564bf8069a1a67
출처 데이터셋
uspto-grants-2011_03
특허 번호
US07902193B2

반응 노트

불러오는 중…