Hydroxylamine → Methyl 4-[amino(hydroxyimino)methyl]-3-fluorobenzoate

HRID 219768Notes

Reaction equation

[C:1]([C:3]1[CH:12]=[CH:11][C:6]([C:7]([O:9][CH3:10])=[O:8])=[CH:5][C:4]=1[F:13])#[N:2].[NH2:14][OH:15]>CCO>[NH2:2][C:1](=[N:14][OH:15])[C:3]1[CH:12]=[CH:11][C:6]([C:7]([O:9][CH3:10])=[O:8])=[CH:5][C:4]=1[F:13]

Participants

Conditions

Temperature: 74 °C

Procedure

To a solution of methyl 4-cyano-3-fluorobenzoate obtained in Step 1 (834.5 mg; 4.66 mmol) in EtOH (9 mL) was added hydroxylamine (50% in water, 1.37 mL; 23.29 mmol). The solution was stirred at 74° C. for 4 h. The solvents were evaporated and the residue was taken in EtOAc (20 mL), washed with brine (3×15 mL), dried over MgSO4 and evaporated, affording the title compound as a yellow solid. 1H NMR: (DMSO-d6, 300 MHz) δ 9.89 (s, 1H), 7.92 (t, J=7.91 Hz, 1H), 7.69 (dd, J=1.70 Hz, J=8.10 Hz, 1H), 7.64 (dd, J=1.51 Hz, J=12.81 Hz, 1H), 5.97 (s, 2H), 3.92 (s, 3H). HPLC (Method A) Rt 2.90 min (Purity: 90.3%).

Workup

customThe solvents were evaporated
washwashed with brine (3×15 mL)
dry with materialdried over MgSO4
customevaporated

Sources & evidence

ORD record: ord-f00667c7ccf14604b73efec5a8f30edd
Source dataset: uspto-grants-2012_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08202865B2

Reaction notes

Loading…