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

HRID 1892444Notes

Reaction equation

C[O:2][C:3](=O)[CH2:4][C:5]1[C:6]([F:16])=[C:7]2[C:12](=[CH:13][C:14]=1[F:15])[N:11]=[CH:10][CH:9]=[CH:8]2.O.[NH2:19][NH2:20]>C(O)C>[F:16][C:6]1[C:5]([CH2:4][C:3]([NH:19][NH2:20])=[O:2])=[C:14]([F:15])[CH:13]=[C:12]2[C:7]=1[CH:8]=[CH:9][CH:10]=[N:11]2

Participants

Conditions

Temperature: 30 °C

Procedure

To a solution of (5,7-difluoro-quinolin-6-yl)-acetic acid methyl ester (1.023 g, 4.32 mmol) in ethanol (15 mL) was added hydrazine monohydrate (2 mL) and the mixture was stirred at 30° C. for 24 h. The solvent was removed in vacuo to afford 1.024 g of the title compound as white solid, which was used without further purification. 1H-NMR (400 MHz, DMSO-d6) δ ppm 9.33 (s, 1H), 8.97 (d, 1H), 8.46 (d, 1H), 7.67 (d, 1H), 7.61 (dd, 1H), 4.27 (s, 2H). LCMS (method A): [MH]+=238, tR=3.24 min. (5,7-difluoroquinolin-6-yl)-acetic acid methyl ester was synthesized using the method described in WO2008/144767 p 108 (intermediate 2), followed by the method described for Intermediate 12, step 1 WO2008/144767 p 114.

Workup

customThe solvent was removed in vacuo

Sources & evidence

ORD record: ord-133b6d889a8d41a8b965d533cc68e6a2
Source dataset: uspto-grants-2013_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08507676B2

Reaction notes

Loading…