Hydrazine hydrate (1:1) → 2-(5,7-Difluoro-quinolin-6-yl)-propionic acid hydrazide

HRID 1892398Notes

Reaction equation

C[O:2][C:3](=O)[CH:4]([C:6]1[C:7]([F:17])=[C:8]2[C:13](=[CH:14][C:15]=1[F:16])[N:12]=[CH:11][CH:10]=[CH:9]2)[CH3:5].O.[NH2:20][NH2:21]>C(O)C>[F:17][C:7]1[C:6]([CH:4]([CH3:5])[C:3]([NH:20][NH2:21])=[O:2])=[C:15]([F:16])[CH:14]=[C:13]2[C:8]=1[CH:9]=[CH:10][CH:11]=[N:12]2

Participants

Conditions

Temperature: 25 °C

Procedure

2-(5,7-Difluoro-quinolin-6-yl)-propionic acid methyl ester (2.270 g, 9.57 mmol) in ethanol (25 mL) was added hydrazine monohydrate (3 mL, 96 mmol), and the reaction mixture was stirred at 25° C. overnight. Solvent was removed under reduced pressure, and the residue was used without further purification. 1H-NMR (400 MHz, DMSO-d6) δ ppm 9.06 (s, 1H), 8.97 (dd, 1H), 8.45 (d, 1H), 7.58-7.67 (m, 2H), 4.23 (br s, 2H), 4.08 (q, 1H), 1.51 (d, 3H). LCMS (method A): [MH]+=252, tR=3.82 min.

Workup

customSolvent was removed under reduced pressure
customthe residue was used without further purification

Sources & evidence

ORD record: ord-08dcb12ffd414173a2349570873c00df
Source dataset: uspto-grants-2013_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08507676B2

Reaction notes

Loading…