Hydrochloric Acid → HCID 76540792, compound

HRID 1960382Notes

Reaction equation

HRID 1960382 reaction equation
[OH: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.[Na+].[CH3:17][CH:18](C(C)=O)[C:19]([O:21][CH2:22][CH3:23])=[O:20].[OH-].[K+]>O.C(O)C.C(#N)C>[OH:1][C:2]1[CH:8]=[CH:7][C:5]([NH:6][N:13]=[C:18]([CH3:17])[C:19]([O:21][CH2:22][CH3:23])=[O:20])=[C:4]([N+:9]([O-:11])=[O:10])[CH:3]=1

Participants

9

Reactant 5

HCID 313Hydrochloric Acid2×HCID 701Ethyl 2-methylacetoacetateHCID 14797Potassium HydroxideHCID 37588824-Amino-3-NitrophenolHCID 23668193Sodium Nitrite

Product 1

HCID 76540792HCID 76540792, compoundYield 57%

Reagents, catalysts & solvents 3

HCID 702EthanolSolventHCID 962WaterSolvent2×HCID 6342AcetonitrileSolvent

Conditions

Temperature
0 °C

Procedure

To a mixture of 4-hydroxy-2-nitroaniline (5.0 g), 1N hydrochloric acid (65 mL) and acetonitrile (20 mL) was added dropwise an aqueous solution (10 mL) of sodium nitrite (2.44 g) at 0-5° C., and the reaction mixture was stirred at 0° C. for 10 min. This mixture was added dropwise to a mixture of ethyl 2-methylacetoacetate (5.61 g), 85% potassium hydroxide (4.37 g), ethanol (50 mL) and water (50 mL) at 0-5° C. After the completion of the dropwise addition, 1N hydrochloric acid (13 mL) and water were added, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine, dried (MgSO4), and concentrated. The obtained residue was washed with hexane to give the title compound (4.94 g, yield 57%) as brown crystals.

Workup

  1. additionwere added
  2. extractionthe mixture was extracted with ethyl acetate
  3. washThe organic layer was washed with saturated brine
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated
  6. washThe obtained residue was washed with hexane

Sources & evidence

ORD record
ord-199a2ccf2cf74303a2ee1393ddb18aaf
Source dataset
uspto-grants-2013_04
Patent number
US08410087B2

Reaction notes

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