Sodium Bicarbonate → 1-[(cyclopropylmethyl)amino]-4-hydroxyquinolin-2(1H)-one

HRID 552096Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 552096
[NH2:1][N:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5]([OH:12])=[CH:4][C:3]1=[O:13].[CH2:14]1[CH:16]([CH:17](O)C#N)[CH2:15]1.C([BH3-])#N.[Na+].C(=O)(O)[O-].[Na+]>CO.[Cl-].[Na+].O.C(O)(=O)C>[CH:16]1([CH2:17][NH:1][N:2]2[C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[C:5]([OH:12])=[CH:4][C:3]2=[O:13])[CH2:14][CH2:15]1

Komponenten

8

Edukt 4

HCID 516892Sodium BicarbonateHCID 5003444Sodium cyanoborohydrideHCID 113893592-Cyclopropyl-2-hydroxyacetonitrileHCID 591688071-amino-4-hydroxyquinolin-2(1H)-one

Produkt 1

HCID 670640181-[(cyclopropylmethyl)amino]-4-hydroxyquinolin-2(1H)-one

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 176Acetic AcidLösungsmittelHCID 887MethanolLösungsmittelHCID 57417360Sodium chloride; waterLösungsmittel

Versuchsvorschrift

To the suspension of 1-amino-4-hydroxyquinolin-2(1H)-one (1.033 g, 5.86 mmol) in methanol (58 mL) was added acetic acid (0.29 mL) and cyclopropylcarboxaldehyde (482 □L, 6.45 mmol) followed by the addition of sodium cyanoborohydride (744.6 mg, 11.85 mmol) at room temperature. The suspension was stirred at room temperature overnight and quenched with half saturated brine (100 mL) and sodium bicarbonate (425 mg, 5.06 mmol). The mixture was extracted with ethyl acetate (300 mL) and the organic layer was separated and washed with half saturated brine (2×50 mL). The combined aqueous layers were extracted with dichloromethane (2×100 mL). The combined organic solution was dried with magnesium sulfate, filtered and concentrated, to give (1-[(cyclopropylmethyl)amino]-4-hydroxyquinolin-2(1H)-one) which was used without any purification. 1H NMR (300 MHz, DMSO-d6) δ 0.09 (m, 2 H) 0.40 (m, 2 H) 0.95 (m, 1 H) 2.70 (t, J=6.43 Hz, 2 H) 5.91 (s, 1 H) 6.10 (t, J=6.07 Hz, 1 H) 7.21 (m, 1 H) 7.62 (t, J=7.17 Hz, 1 H) 7.87 (m, 2 H) 11.42 (br s, 1 H).

Aufarbeitung

  1. extractionThe mixture was extracted with ethyl acetate (300 mL)
  2. customthe organic layer was separated
  3. washwashed with half saturated brine (2×50 mL)
  4. extractionThe combined aqueous layers were extracted with dichloromethane (2×100 mL)
  5. dry with materialThe combined organic solution was dried with magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-623eca8055ea455a8474996d05de8740
Quelldatensatz
uspto-grants-2011_05
Patentnummer
US07951800B2

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