Hydrochloric Acid → HCID 72321882, compound

HRID 1802797Notes

Reaction equation

HRID 1802797 reaction equation
[F:1][C:2]1[CH:8]=[CH:7][C:5]([NH2:6])=[C:4]([N+:9]([O-:11])=[O:10])[CH:3]=1.Cl.[N+:13]([O-])([O-])=O.[Na+].[CH3:18][CH:19](C(C)=O)[C:20]([O:22][CH2:23][CH3:24])=[O:21].[OH-].[Na+]>O.C(O)C>[CH2:23]([O:22][C:20](=[O:21])[C:19](=[N:13][NH:6][C:5]1[CH:7]=[CH:8][C:2]([F:1])=[CH:3][C:4]=1[N+:9]([O-:11])=[O:10])[CH3:18])[CH3:24]

Participants

8

Reactant 5

HCID 313Hydrochloric AcidHCID 701Ethyl 2-methylacetoacetateHCID 14798Sodium HydroxideHCID 24268Sodium NitrateHCID 677694-Fluoro-2-nitroaniline

Product 1

HCID 72321882HCID 72321882, compoundYield 46%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent2×

Procedure

4-Fluoro-2-nitroaniline (10 g, 64 mmol) was dissolved in 6N hydrochloric acid (64 ml, 0.27 mol), sodium nitrate (4.4 g, 64 mmol) dissolved in water (50 ml) was slowly added in drops at 0° C., and the mixture was stirred for 30 min at 0° C.˜room temperature. At the same time, ethyl 2-methylacetoacetate (9.2 ml, 64 mmol) and sodium hydroxide (19 g, 0.34 mol) were dissolved in 80% ethanol aqueous solution (95 ml) and stirred for 10 min at 0° C. Thus prepared two solutions were mixed and stirred for 8 h at 0° C.˜room temperature. To the reaction mixture was added water. The solid not dissolved was collected, washed with water and dried to give the title compound (7.9 g, Yield 46%).

Workup

  1. additionwas slowly added in drops at 0° C.
  2. stirringstirred for 10 min at 0° C
  3. customThus prepared two solutions
  4. additionwere mixed
  5. stirringstirred for 8 h at 0° C.˜room temperature
  6. dissolutionThe solid not dissolved
  7. customwas collected
  8. washwashed with water
  9. customdried

Sources & evidence

ORD record
ord-e34920ce22224371abf39c87a5a2dbeb
Source dataset
uspto-grants-2013_01
Patent number
US08349885B2

Reaction notes

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