Acetonitrile → 2-Amino-n-(1,4-dioxo-1,2,3,4-tetrahydrophthalazin-5-yl)acetamide

HRID 241487Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 241487
Cl[CH2:2][C:3]([NH:5][C:6]1[CH:15]=[CH:14][CH:13]=[C:12]2[C:7]=1[C:8](=[O:17])[NH:9][NH:10][C:11]2=[O:16])=[O:4].C(#[N:20])C>[OH-].[NH4+].O>[NH2:20][CH2:2][C:3]([NH:5][C:6]1[CH:15]=[CH:14][CH:13]=[C:12]2[C:7]=1[C:8](=[O:17])[NH:9][NH:10][C:11]2=[O:16])=[O:4]

Komponenten

5

Edukt 2

HCID 6342AcetonitrileHCID 543576732-Chloro-N-(1,4-dioxo-1,2,3,4-tetrahydrophthalazine-5-yl)acetamide

Produkt 1

HCID 247112532-Amino-n-(1,4-dioxo-1,2,3,4-tetrahydrophthalazin-5-yl)acetamide

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittel2×HCID 14923Ammonium HydroxideLösungsmittel

Versuchsvorschrift

2-Chloro-N-(1,4-dioxo-1,2,3,4-tetrahydrophthalazine-5-yl)acetamide (300 mg; 1.182 mmol) was suspended in ammonium hydroxide (7 ml) and stirred slowly in a vial at 4 C for 8 days (30%). The reaction mixture was transferred into a flask and hot water (25 ml) was added to the reaction mixture, filtered, and the filtrate was collected. The initial pH (12) of the filtrate was adjusted to 5.38 by slow addition of acetic acid to obtain the intermediate. The beige colored solid was filtered, rinse with water (10 ml), washed with methanol (50 mL), and finally with ether (50 ml), and then dried under reduced pressure. The residue was suspended in hydrazine (30% in water, 22 ml) and heated to dissolve the precipitates. The contents were allowed to cool to RT, pH was adjusted to 4.8, and precipitates were obtained upon cooling. The resultant precipitates were filtered, washed with water, methanol (cold), ether, and then dried under reduced pressure to obtain 2. 1H NMR (300 MHz, DMSO-d6) δ: 8.86 (d, 1H), 7.85 (t, 1H), 7.60 (d, 1H), 3.33 (s, 2H), 2.16 (s, 3H, Methyl for Acetic Acid); ESMS: Calcd for C10H10N4O3: 234.0, Found, 235.0; HPLC: Purity was further analyzed on a C-18 column (Vydac) employing a mobile phase eluent gradient of 10-90% acetonitrile in water containing 0.1% TFA over 30 minutes with a flow rate of 1 mL/min, Rt=13.2 min.

Aufarbeitung

  1. customThe reaction mixture was transferred into a flask
  2. filtrationfiltered
  3. customthe filtrate was collected
  4. additionThe initial pH (12) of the filtrate was adjusted to 5.38 by slow addition of acetic acid
  5. customto obtain the intermediate
  6. filtrationThe beige colored solid was filtered
  7. washrinse with water (10 ml)
  8. washwashed with methanol (50 mL)
  9. dry with materialfinally with ether (50 ml), and then dried under reduced pressure
  10. temperatureheated
  11. dissolutionto dissolve the precipitates
  12. customprecipitates
  13. customwere obtained
  14. temperatureupon cooling
  15. customThe resultant precipitates
  16. filtrationwere filtered
  17. washwashed with water, methanol (cold), ether
  18. customdried under reduced pressure
  19. customto obtain 2
  20. customover 30 minutes

Quellen und Nachweise

ORD-Eintrag
ord-d78869083ff74465828b57d6a0973594
Quelldatensatz
uspto-grants-2014_02
Patentnummer
US08652442B2

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