Hydrochloric Acid → HCID 178496278, compound

HRID 1895116Notes

Reaction equation

[N:1]([O-])=O.[Na+].[F:5][C:6]1[CH:12]=[C:11]([I:13])[CH:10]=[CH:9][C:7]=1[NH2:8].Cl.[CH3:15][O:16][CH2:17][C:18](=[O:24])[CH2:19][C:20]([O:22][CH3:23])=[O:21].CC([O-])=O.[Na+]>O.CO>[F:5][C:6]1[CH:12]=[C:11]([I:13])[CH:10]=[CH:9][C:7]=1[NH:8][N:1]=[C:19]([C:18](=[O:24])[CH2:17][O:16][CH3:15])[C:20]([O:22][CH3:23])=[O:21]

Participants

Conditions

Temperature: 0 °C

Procedure

A solution of NaNO2 (1.66 g, 24 mmol) in H2O (5 mL) was added dropwise at 0° C. to a mixture of 2-fluoro-4-iodoaniline (4.74 g, 20 mmol) and 6 M HCl aqueous solution (20 mL, 120 mmol). After stirring for 15 min, the resulting aqueous solution was added to a suspension of methyl 4-methoxyacetoacetate (2.59 mL, 20 mmol) and NaOAc (9.84 g, 120 mmol) in MeOH (40 mL) pre-cooled at 0° C. The reaction mixture was poured into water and extracted with AcOEt. The extract was washed with saturated NaHCO3 aqueous solution and brine, dried over MgSO4, and concentrated under reduced pressure. The residue was recrystallized from hexane/AcOEt to give the title compound (6.29 g, 80% yield) as yellow crystals: mp 141-146° C.; 1H NMR (300 MHz, CDCl3): δ ppm 3.50 (3H, s), 3.93 (3H, s), 4.64 (2H, s), 7.35 (1H, t, J=8.5 Hz), 7.49-7.55 (2H, m), 12.97 (1H, br s). Anal. Calcd for C12H12FIN2O4: C, 36.57; H, 3.07; N, 7.11. Found: C, 36.74; H, 3.10; N, 7.32.

Workup

extractionextracted with AcOEt
washThe extract was washed with saturated NaHCO3 aqueous solution and brine
dry with materialdried over MgSO4
concentrationconcentrated under reduced pressure
customThe residue was recrystallized from hexane/AcOEt

Sources & evidence

ORD record: ord-ebfed1074bf54762ba1aeaa249e37420
Source dataset: uspto-grants-2013_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08513251B2

Reaction notes

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