Lithium Hydroxide → 6-Chloro-4-(isopropylamino)nicotinic acid

HRID 595385

Reaktionsgleichung

Reaktionsgleichung von HRID 595385
[Cl:1][C:2]1[CH:12]=[C:11]([NH:13][CH:14]2[CH2:17]C[CH2:15]2)[C:5]([C:6]([O:8]CC)=[O:7])=[CH:4][N:3]=1.[Li+].[OH-]>C(O)C.O>[Cl:1][C:2]1[CH:12]=[C:11]([NH:13][CH:14]([CH3:17])[CH3:15])[C:5]([C:6]([OH:8])=[O:7])=[CH:4][N:3]=1

Komponenten

5

Edukt 2

HCID 3939Lithium HydroxideHCID 89689654Ethyl 6-chloro-4-(cyclobutylamino)nicotinate

Produkt 1

HCID 896898576-Chloro-4-(isopropylamino)nicotinic acid

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 702EthanolLösungsmittelHCID 962WaterLösungsmittel

Versuchsvorschrift

Ethyl 6-chloro-4-(cyclobutylamino)nicotinate (2) (3 g, 12.3 mmol) in ethanol (20 mL) and water (10 mL) was stirred at rt. LiOH (61.7 mmol, 5 equiv.) was added and the reaction mixture was stirred at room temperature for 4 h. The solvent was concentrated under reduced pressure. Diluted with EtOAc and added water. The aqueous layer was collected and acidified to pH 3-4 using solid citric acid. Solid material precipitated out. Filtered the solid material and dried under vacuum to furnish the title compound (3). 1H NMR: 400 MHz, DMSO-d6: δ 1.20 (d, J=6.40 Hz, 6H), 3.80-3.88 (m, 1H), 6.80 (s, 1H), 8.20 (d, J=7.60 Hz, 1H), 8.51 (s, 1H), 13.33 (bs, 1H).

Aufarbeitung

  1. concentrationThe solvent was concentrated under reduced pressure
  2. additionDiluted with EtOAc
  3. additionadded water
  4. customThe aqueous layer was collected
  5. customSolid material precipitated out
  6. filtrationFiltered the solid material
  7. customdried under vacuum

Quellen und Nachweise

ORD-Eintrag
ord-7d3cfcf1f3eb4193ae15f915ff681a51
Quelldatensatz
uspto-grants-2016_01
Patentnummer
US09242975B2

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