(2,4-dimethylphenyl)hydrazine → HCID 178426279, compound

HRID 1600053Notes

Reaction equation

HRID 1600053 reaction equation
[C:1]([C:5]1[C:6]([C:18](Cl)=[O:19])=[N:7][C:8]2[C:13]([C:14]=1[OH:15])=[C:12]([Cl:16])[CH:11]=[C:10]([Cl:17])[CH:9]=2)([O:3]C)=O.[CH3:21][C:22]1[CH:27]=[C:26]([CH3:28])[CH:25]=[CH:24][C:23]=1[NH:29][NH2:30]>O1CCCC1>[Cl:17][C:10]1[CH:11]=[C:12]([Cl:16])[C:13]2[C:14](=[O:15])[C:5]3[C:1](=[O:3])[N:29]([C:23]4[CH:24]=[CH:25][C:26]([CH3:28])=[CH:27][C:22]=4[CH3:21])[N:30]=[C:18]([OH:19])[C:6]=3[NH:7][C:8]=2[CH:9]=1

Participants

4

Reactant 2

HCID 702862(2,4-dimethylphenyl)hydrazineHCID 178498567HCID 178498567, compound

Product 1

HCID 178426279HCID 178426279, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

3-Carbomethoxy-5,7-dichloro-4-hydroxyquinoline-2-carbonyl chloride (3.65 g,11.0 mM) was dissolved in tetrahydrofuran (274 mL) and added dropwise to a cooled (0° C.) solution of 2,4-dimethylphenylhydrazine (3.13 g, 23.0 mM) in tetrahydrofuran (172 mL) with stirring. A brown/red suspensionslowly formed and the resulting mixture was stirred at 0° C. for 30 min. The reaction was quenched by adding cold water (223 mL) followed by 1N HCl (669 mL). The resulting mixture was stirred for 1 hr and then filtered to separate the precipitated solids. The collected solids were washed with water and then ether to provide, after air drying, the title compound (3.60 g, 76%) as a white powder; MS(CI): 434 (M+H).

Workup

  1. additionadded dropwise to
  2. customA brown/red suspensionslowly formed
  3. stirringthe resulting mixture was stirred at 0° C. for 30 min
  4. customThe reaction was quenched
  5. additionby adding cold water (223 mL)
  6. stirringThe resulting mixture was stirred for 1 hr
  7. filtrationfiltered
  8. customto separate the precipitated solids
  9. washThe collected solids were washed with water
  10. customether to provide
  11. customafter air drying

Sources & evidence

ORD record
ord-ba7d90c28a7846208f1d543c63d8d739
Source dataset
uspto-grants-1998_04
Patent number
US05744471

Reaction notes

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