Hydrazine hydrate (1:1) → 2,2-Difluoro-2-(quinolin-6-yl)acetohydrazide

HRID 456061Notes

Reaction equation

C([O:3][C:4](=O)[C:5]([F:17])([F:16])[C:6]1[CH:7]=[C:8]2[C:13](=[CH:14][CH:15]=1)[N:12]=[CH:11][CH:10]=[CH:9]2)C.[NH2:19][NH2:20].O>CO>[F:16][C:5]([F:17])([C:6]1[CH:7]=[C:8]2[C:13](=[CH:14][CH:15]=1)[N:12]=[CH:11][CH:10]=[CH:9]2)[C:4]([NH:19][NH2:20])=[O:3]

Participants

Conditions

Temperature: 45 °C

Procedure

Difluoro-quinolin-6-yl-acetic acid ethyl ester (836 mg, 3.33 mmol) was dissolved in MeOH (13 ml). Hydrate hydrazine (1.5 ml, 16.8 mmol) was added in the reaction mixture. The mixture was heated to 45° C. for 30 min, cooled to room temperature, concentrated, and taken up in DCM. The organic layer was dried over MgSO4, filtered and concentrated in vacuo to give the crude product, which was purified by silica gel column to give difluoro-quinolin-6-yl-acetic acid hydrazide as a light orange solid (400 mg, 51%), 1H-NMR (CDCl3) δ ppm 3.99 (brs, 2H); 7.51 (m, 1H); 7.92 (m, 1H); 8.15 (s, 1H); 8.20-8.26 (q, 2H); 9.02 (m, 1H).

Workup

temperaturecooled to room temperature
concentrationconcentrated
dry with materialThe organic layer was dried over MgSO4
filtrationfiltered
concentrationconcentrated in vacuo
customto give the crude product, which
customwas purified by silica gel column

Sources & evidence

ORD record: ord-839e9485cf774b72a29911656a3c4e53
Source dataset: uspto-grants-2013_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08497368B2

Reaction notes

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