Water → HCID 178422993, compound

HRID 1196895Notes

Reaction equation

HRID 1196895 reaction equation
[CH3:1][C:2]1[CH:6]=[C:5]([CH:7]=O)[NH:4][N:3]=1.S([O-])(O)=O.[Na+].O.[CH3:15][C:16]1([CH3:29])[C:25]2[C:20](=[CH:21][C:22]([NH2:27])=[C:23]([NH2:26])[CH:24]=2)[NH:19][C:18](=[O:28])[CH2:17]1>C(O)C>[CH3:15][C:16]1([CH3:29])[C:25]2[CH:24]=[C:23]3[NH:26][C:7]([C:5]4[NH:4][N:3]=[C:2]([CH3:1])[CH:6]=4)=[N:27][C:22]3=[CH:21][C:20]=2[NH:19][C:18](=[O:28])[CH2:17]1

Participants

6

Reactant 4

HCID 962WaterHCID 19896766HCID 19896766, compoundHCID 23665763Sodium BisulfiteHCID 178427211HCID 178427211, compound

Product 1

HCID 178422993HCID 178422993, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

1.5 g. (13.6 mmole) 3-methyl-1H-pyrazole-5-aldehyde was stirred with 4.5 g. sodium hydrogen sulphite in 9 ml. water for 3 hours at 60° C. The evaporation residue was stirred with 2.79 g. (13.6 mmole) 4,4-dimethyl-6,7-diamino-1,2,3,4-tetrahydroquinolin-2-one and 40 ml. ethanol for 3 hours at 60° C. while passing through air. Half of the ethanol was distilled off, water was added and the residue was filtered off with suction and recrystallized from ethyl acetate/methanol to give 3.3 g. (82.5% of theory) of the title compound; m.p. 242°-245° C.

Workup

  1. distillationHalf of the ethanol was distilled off
  2. additionwater was added
  3. filtrationthe residue was filtered off with suction
  4. customrecrystallized from ethyl acetate/methanol
  5. customto give 3.3 g

Sources & evidence

ORD record
ord-a05fd6c2907f4cddbe130919066d60aa
Source dataset
uspto-grants-1992_05
Patent number
US05116843

Reaction notes

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