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

HRID 23821Notes

Reaction equation

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

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 (0.4 mL) was added to a solution of 2,5-dichloro-N-(2-hydroxyamino-ethyl)-benzamide (0.28 g, 1.1 mmol) in pyridine (10 mL) at 0° C. under an argon atmosphere. The reaction mixture was stirred for 2 h and the pyridine removed in vacuo. The residue was purified by preparative reverse-phase HPLC to provide the title compound (0.1 g, 33%) as a white solid. 1H NMR* (400 MHz, CD3OD): δ 8.35 (s, 0.5H); 7.95 (s, 0.5H); 7.45 (m, 3H); 3.78 (m, 1H); 3.73 (m, 1H); 3.62 (m, 2H). * 1:1 mixture of rotamers. ESMS: M+H=277.

Workup

customthe pyridine removed in vacuo
customThe residue was purified by preparative reverse-phase HPLC

Sources & evidence

ORD record: ord-cf7a974f56e34a21bbc47ea7321b2f71
Source dataset: uspto-grants-2005_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06852882B2

Reaction notes

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