Hydrochloric Acid → HCID 72321882, compound

HRID 1876303Notes

Reaction equation

HRID 1876303 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×

Conditions

Temperature
0 °C

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 thereto at 0° C., and the mixture was stirred for 30 min at 0° C.˜room temperature. Simultaneously, ethyl 2-methylacetoacetate (9.2 ml, 64 mmol) and sodium hydroxide (19 g, 0.34 mol) were dissolved in 80% aqueous ethanol solution (95 ml), and stirred for 10 min at 0° C. The two solutions thus prepared were mixed, and stirred for 8 h at 0° C.˜room temperature. Water was added to the reaction solution, and the insoluble solid was collected. The solid was washed with water, and dried to give the title compound (7.9 g, Yield 46%).

Workup

  1. additionwas slowly added in drops
  2. stirringstirred for 10 min at 0° C
  3. customThe two solutions thus prepared
  4. additionwere mixed
  5. stirringstirred for 8 h at 0° C.˜room temperature
  6. customthe insoluble solid was collected
  7. washThe solid was washed with water
  8. customdried

Sources & evidence

ORD record
ord-548d161ad63d41d7a20840bbcb1d6eb9
Source dataset
uspto-grants-2012_11
Patent number
US08309586B2

Reaction notes

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