Ammonia → HCID 9796059, compound

HRID 36398Notes

Reaction equation

HRID 36398 reaction equation
[C:1]1([NH2:8])[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[NH2:7].[CH3:9][C:10]1([CH3:24])[C:19]2[C:14](=[CH:15][C:16]([C:20](O)=O)=[CH:17][CH:18]=2)[NH:13][C:12](=[O:23])[CH2:11]1.N>O=P12OP3(OP(OP(O3)(O1)=O)(=O)O2)=O.O.C(O)C>[CH3:9][C:10]1([CH3:24])[C:19]2[C:14](=[CH:15][C:16]([C:20]3[NH:7][C:2]4[CH:3]=[CH:4][CH:5]=[CH:6][C:1]=4[N:8]=3)=[CH:17][CH:18]=2)[NH:13][C:12](=[O:23])[CH2:11]1

Participants

7

Reactant 3

HCID 222AmmoniaHCID 7243O-PhenylenediamineHCID 150777994,4-Dimethyl-1,2,3,4-tetrahydro-2-oxo-7-quinolinecarboxylic acid

Product 1

HCID 9796059HCID 9796059, compoundYield 37.2%

Reagents, catalysts & solvents 3

HCID 702EthanolSolventHCID 962WaterSolvent2×HCID 14812Phosphorus oxide (P4O10)Solvent

Procedure

One stirs ortho-phenylenediamine (1.30 g, 12.0 mmol) and 4,4-dimethyl-1,2,3,4-tetrahydro-2-oxo-7-quinolinecarboxylic acid (2.60 g, 12.0 mmol; preparation see DE-A-3,818,830) in a mixture of polyphosphoric acid (50 g) and diphosphorus pentoxide (10 g) for 3 hours at 160° C. One allows to cool to 80°-90° C., carefully adds ice and water thereto and filters off the precipitate with suction. One takes up in water (200 ml), adds conc. ammonia thereto, filters off with suction, dissolves the residue in hot ethanol, filters and allows to crystallise. One dries the colourless crystals at 120° C. in a vacuum and obtains 1.30 g (37%) of the title compound with the m.p. 314°-316° C. which, per mole, still has adhering a half mol of water.

Workup

  1. temperatureto cool to 80°-90° C.
  2. customto crystallise
  3. customat 120° C.

Sources & evidence

ORD record
ord-1e8453bbd40d465e9029859281e7c2cb
Source dataset
uspto-grants-1995_05
Patent number
US05414088

Reaction notes

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