Ammonia → HCID 67775530, compound

HRID 533424Notes

Reaction equation

HRID 533424 reaction equation
O=P12OP3(OP(OP(O3)(O1)=O)(=O)O2)=O.P(=O)(O)(O)O.[NH2:20][C:21]1[CH:30]=[CH:29][C:24]([C:25]([O:27][CH3:28])=[O:26])=[CH:23][C:22]=1[CH3:31].[C:32](OCC)(=[O:37])[CH2:33][C:34]([CH3:36])=O.N>O>[CH3:36][C:34]1[NH:20][C:21]2[C:30]([C:32](=[O:37])[CH:33]=1)=[CH:29][C:24]([C:25]([O:27][CH3:28])=[O:26])=[CH:23][C:22]=2[CH3:31]

Participants

7

Reactant 5

HCID 222AmmoniaHCID 1004Phosphoric AcidHCID 8868Ethyl AcetoacetateHCID 14812Phosphorus oxide (P4O10)HCID 2736799Methyl 4-amino-3-methylbenzoate

Product 1

HCID 67775530HCID 67775530, compoundYield 42.9%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
140 °C

Procedure

A mixture of phosphorus pentoxide (37 g) and phosphoric acid (46 g) was heated under stirring in an oil bath at 140° C., and methyl 4-amino-3-methylbenzoate (3.0 g) and ethyl acetoacetate (2.8 g) were added thereto, followed by heating under stirring for an additional 2 hours. The reaction mixture was cooled to 60° C., poured into water, and neutralized with a 29% aqueous ammonia solution, and the precipitate was collected by filtration to obtain methyl 2,8-dimethyl-4-oxo-1,4-dihydroquinoline-6-carboxylate (1.8 g).

Workup

  1. temperaturewas heated
  2. temperatureby heating
  3. stirringunder stirring for an additional 2 hours
  4. temperatureThe reaction mixture was cooled to 60° C.
  5. filtrationthe precipitate was collected by filtration

Sources & evidence

ORD record
ord-35d0cfa5957d41579cd566f3ad6da135
Source dataset
uspto-grants-2014_10
Patent number
US08853242B2

Reaction notes

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