2-Fluoroaniline → HCID 86030630, compound

HRID 968672Notes

Reaction equation

HRID 968672 reaction equation
[N:1]([O-])=O.[Na+].[F:5][C:6]1[CH:12]=[CH:11][CH:10]=[CH:9][C:7]=1[NH2:8].[Cl:13][CH2:14][C:15](=[O:22])[CH2:16][C:17]([O:19][CH2:20][CH3:21])=[O:18].CC([O-])=O.[Na+]>OS(O)(=O)=O.CC(O)=O.O>[Cl:13][CH2:14][C:15](=[O:22])[CH:16]([N:1]=[N:8][C:7]1[CH:9]=[CH:10][CH:11]=[CH:12][C:6]=1[F:5])[C:17]([O:19][CH2:20][CH3:21])=[O:18]

Participants

8

Reactant 4

HCID 95842-FluoroanilineHCID 69484Ethyl 4-chloroacetoacetateHCID 517045Sodium AcetateHCID 23668193Sodium Nitrite

Product 1

HCID 86030630HCID 86030630, compoundYield 73.1%

Reagents, catalysts & solvents 3

HCID 176Acetic AcidSolvent2×HCID 962WaterSolvent2×HCID 1118Sulfuric AcidSolvent

Conditions

Temperature
0 °C

Procedure

A solution of NaNO2 (0.96 g) in conc. H2SO4 (4 mL) was added to a solution of 2-fluoroaniline (1.52 g) in AcOH (23 mL) at 0° C., and the mixture was stirred for 1 hour at 0° C. The reaction mixture was added to a solution of ethyl 4-chloro-3-oxobutanoate (2.16 g) in a mixture of AcOH (10 mL) and H2O (20 mL) at 0° C. and the reaction mixture was stirred for 15 minutes at 0° C. A solution of NaOAc (12.2 g) in H2O (20 mL) was added to the reaction mixture at 0° C., and the reaction mixture was stirred for 1 hour at room temperature to produce a precipitate. The precipitate was collected by filtration and washed with H2O to yield 2.75 g of the title compound. AcOH and NaOAc means acetic acid and sodium acetate, respectively.

Workup

  1. stirringthe reaction mixture was stirred for 15 minutes at 0° C
  2. stirringthe reaction mixture was stirred for 1 hour at room temperature
  3. customto produce a precipitate
  4. filtrationThe precipitate was collected by filtration
  5. washwashed with H2O

Sources & evidence

ORD record
ord-a21066dcf6c945559e43a7a8b69aff14
Source dataset
uspto-grants-2007_12
Patent number
US07304072B2

Reaction notes

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