Methyl 4-methoxyacetoacetate → HCID 178496286, compound

HRID 1895178

Reaction equation

HRID 1895178 reaction equation
[F:1][C:2]1[CH:8]=[CH:7][C:6]([I:9])=[CH:5][C:3]=1[NH2:4].[N:10]([O-])=O.[Na+].[CH3:14][O:15][CH2:16][C:17](=[O:23])[CH2:18][C:19]([O:21][CH3:22])=[O:20].CC([O-])=O.[Na+]>Cl.O.CCO>[F:1][C:2]1[CH:8]=[CH:7][C:6]([I:9])=[CH:5][C:3]=1[NH:4][N:10]=[C:18]([C:17](=[O:23])[CH2:16][O:15][CH3:14])[C:19]([O:21][CH3:22])=[O:20]

Participants

8

Reactant 4

HCID 123500Methyl 4-methoxyacetoacetateHCID 517045Sodium AcetateHCID 23668193Sodium NitriteHCID 254184602-Fluoro-5-iodoaniline

Product 1

HCID 178496286HCID 178496286, compoundYield 87%

Reagents, catalysts & solvents 3

HCID 313Hydrochloric AcidSolventHCID 702EthanolSolventHCID 962WaterSolvent

Conditions

Temperature
0 °C

Procedure

To a suspension of 2-fluoro-5-iodoaniline (9.83 g, 41.5 mmol) in 6 M HCl aqueous solution (83.0 mL) was added a solution of NaNO2 (3.43 g, 49.8 mmol) in water (8.3 mL) at 0° C. To a suspension of methyl 4-methoxy-3-oxobutanoate (5.37 mL, 41.5 mmol) and NaOAc (124 g) in EtOH (70 mL) was added the above solution at 0° C. The mixture was stirred at 0° C. for 10 min. The precipitates were collected by filtration, washed with water, dissolved in EtOAc, washed with brine, dried over MgSO4, filtered and concentrated in vacuo to yield the title compound (14.2 g, 87% yield) as a red solid: 1H NMR (DMSO-d6, 300 MHz): δ ppm 3.31 (3H, s), 3.83 (3H, s), 4.64 (2H, s), 7.03-7.41 (1H, m), 7.43-7.66 (1H, m), 7.85-8.07 (1H, m), 12.20 (1H, brs).

Workup

  1. additionwas added the above solution at 0° C
  2. filtrationThe precipitates were collected by filtration
  3. washwashed with water
  4. dissolutiondissolved in EtOAc
  5. washwashed with brine
  6. dry with materialdried over MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-04543525e77c43b7b8a892ddd0fe211d
Source dataset
uspto-grants-2013_08
Patent number
US08513251B2

Linked notes

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