Aniline → HCID 178496274, compound

HRID 333734Notes

Reaction equation

HRID 333734 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[N:8]([O-])=O.[Na+].[CH3:12][O:13][CH2:14][C:15](=[O:21])[CH2:16][C:17]([O:19][CH3:20])=[O:18].C([O-])(=O)C.[Na+]>Cl.CO.O.O>[CH3:12][O:13][CH2:14][C:15](=[O:21])[C:16](=[N:8][NH:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)[C:17]([O:19][CH3:20])=[O:18]

Participants

8

Reactant 4

HCID 6115AnilineHCID 123500Methyl 4-methoxyacetoacetateHCID 517045Sodium AcetateHCID 23668193Sodium Nitrite

Product 1

HCID 178496274HCID 178496274, compoundYield 82.8%

Reagents, catalysts & solvents 3

HCID 313Hydrochloric AcidSolventHCID 962WaterSolventHCID 22242641Methanol--water (1/1)Solvent

Procedure

To a solution of aniline (50 g) in 6N hydrochloric acid (536 mL) was added dropwise with stirring under ice-cooling an aqueous solution (142 mL) of sodium nitrite (55.6 g). The solution was added dropwise to a mixed solution of methyl 4-methoxy-3-oxobutanoate (78.5 g) and sodium acetate (264 g) in methanol/water (1.4 L/0.35 L) with stirring under ice-cooling. The total amount was added dropwise, and the mixture was stirred at the same temperature for 2 hr. Water was added to the reaction mixture, and the mixture was stirred for 30 min. The precipitated yellow crystals were collected by filtration, washed successively with water, ethanol/diisopropyl ether (1/9) and diisopropyl ether, and dry to give the title compound (111.2 g) as yellow crystals.

Workup

  1. stirringwith stirring under ice-
  2. temperaturecooling
  3. additionThe total amount was added dropwise
  4. stirringthe mixture was stirred at the same temperature for 2 hr
  5. stirringthe mixture was stirred for 30 min
  6. filtrationThe precipitated yellow crystals were collected by filtration
  7. washwashed successively with water, ethanol/diisopropyl ether (1/9) and diisopropyl ether
  8. customdry

Sources & evidence

ORD record
ord-833a1f557703409a9bf8ba0369bda48c
Source dataset
uspto-grants-2014_11
Patent number
US08883788B2

Reaction notes

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