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

HRID 600270Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 600270
[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

Komponenten

6

Edukt 2

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

Produkt 1

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

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 23925IronKatalysatorHCID 702EthanolLösungsmittelHCID 962WaterLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

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.

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-84f76ef90b654fa28d564bf8069a1a67
Quelldatensatz
uspto-grants-2011_03
Patentnummer
US07902193B2

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