Formic Acid → 5-Bromo-2-chloro-N-[2-(N-formyl-N-hydroxy-amino)-ethyl]-benzamide

HRID 23824Notes

Reaction equation

C(OC(=O)C)(=O)C.[CH:8]([OH:10])=O.[Br:11][C:12]1[CH:13]=[CH:14][C:15]([Cl:25])=[C:16]([CH:24]=1)[C:17]([NH:19][CH2:20][CH2:21][NH:22][OH:23])=[O:18]>N1C=CC=CC=1>[Br:11][C:12]1[CH:13]=[CH:14][C:15]([Cl:25])=[C:16]([CH:24]=1)[C:17]([NH:19][CH2:20][CH2:21][N:22]([CH:8]=[O:10])[OH:23])=[O:18]

Participants

Conditions

Temperature: 0 °C

Procedure

A mixture of acetic anhydride (2 mL) and formic acid (1 mL) was allowed to stand at 55° C. for 2.5 h. After cooling to 0° C., the resulting mixed anhydride (0.5 mL) was added to a solution of 5-bromo-2-chloro-N-(2-hydroxyamino-ethyl)-benzamide (0.7 g, 2.4 mmol) in pyridine (6 mL) at 0° C. under an argon atmosphere. The reaction mixture was stirred for 1 h and the pyridine removed in vacuo. The residue was chased twice with water and twice with MeOH. The resulting solid was washed with ether/acetonitrile (9:1) to provide the title compound (0.42 g, 55%) as a white solid. 1H NMR* (400 MHz, CD3OD): δ 8.35 (s, 0.5H); 7.95 (s, 0.5H); 7.58 (m, 2H); 7.38 (m, 1H); 3.78 (m, 1H); 3.73 (m, 1H); 3.62 (m, 2H). * 1:1 mixture of rotamers. ESMS: M+H=321.

Workup

customthe pyridine removed in vacuo
washThe resulting solid was washed with ether/acetonitrile (9:1)

Sources & evidence

ORD record: ord-c9f97c0f5c424e51a9503dabfb0aca53
Source dataset: uspto-grants-2005_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06852882B2

Reaction notes

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