Ammonia → HCID 19896777, compound

HRID 1196894Notes

Reaction equation

HRID 1196894 reaction equation
[CH3:1][C:2]1([CH3:15])[C:11]2[C:6](=[CH:7][C:8]([NH2:13])=[C:9]([NH2:12])[CH:10]=2)[NH:5][C:4](=[O:14])[CH2:3]1.[N:16]1([C:21]2[CH:28]=[CH:27][C:24]([CH:25]=O)=[CH:23][CH:22]=2)[CH:20]=[CH:19][N:18]=[CH:17]1.C1(C)C=CC(S(O)(=O)=O)=CC=1.N>O.C(O)C>[CH3:1][C:2]1([CH3:15])[C:11]2[CH:10]=[C:9]3[NH:12][C:25]([C:24]4[CH:23]=[CH:22][C:21]([N:16]5[CH:20]=[CH:19][N:18]=[CH:17]5)=[CH:28][CH:27]=4)=[N:13][C:8]3=[CH:7][C:6]=2[NH:5][C:4](=[O:14])[CH2:3]1

Participants

7

Reactant 4

HCID 222AmmoniaHCID 6101p-Toluenesulfonic acidHCID 7365304-(1H-imidazol-1-yl)benzaldehydeHCID 19896766HCID 19896766, compound

Product 1

HCID 19896777HCID 19896777, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

2 g. (9.7 mmole) 4,4-dimethyl-6,7-diamino-1,2,3,4-tetrahydroquinolin-2-one (see Example 13 a)), 1.67 g. (9.7 mmole) 4-(1H-imidazol-1-yl)-benzaldehyde, 0.17 g. p-toluenesulphonic acid and 120 ml. ethanol were mixed together and heated under reflux for 3 hours while passing through air. The evaporation residue was suspended in water, neutralized with 2N aqueous ammonia and recrystallized from methanol to give 1.7 g. (49% of theory) of the title compound; m.p. >300° C.

Workup

  1. temperatureheated
  2. temperatureunder reflux for 3 hours
  3. customrecrystallized from methanol
  4. customto give 1.7 g

Sources & evidence

ORD record
ord-89a3941b641f4bb4ae02497a6d1f11c6
Source dataset
uspto-grants-1992_05
Patent number
US05116843

Reaction notes

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