Hydrochloric Acid → HCID 178439204, compound

HRID 1977212Notes

Reaction equation

HRID 1977212 reaction equation
[Cl:1][C:2]1[CH:11]=[C:10]2[C:5]([C:6]([OH:20])=[C:7]([C:16]([O:18]C)=O)[C:8]([C:12]([O:14]C)=O)=[N:9]2)=[CH:4][CH:3]=1.Cl.[CH:22]([C:25]1[CH:30]=[CH:29][C:28]([NH:31][NH2:32])=[CH:27][CH:26]=1)([CH3:24])[CH3:23].C(N(CC)CC)C.Cl>C(O)C>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[C:6](=[O:20])[C:7]3[C:16]([OH:18])=[N:32][N:31]([C:28]4[CH:29]=[CH:30][C:25]([CH:22]([CH3:24])[CH3:23])=[CH:26][CH:27]=4)[C:12](=[O:14])[C:8]=3[NH:9][C:10]=2[CH:11]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 8471TriethylamineHCID 2733248[4-(Propan-2-yl)phenyl]hydrazine hydrochlorideHCID 178418477HCID 178418477, compound

Product 1

HCID 178439204HCID 178439204, compoundYield 69.3%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a stirred suspension of dimethyl 7-chloro-4-hydroxyquinoline-2,3-dicarboxylate (2.01 g, 6.80 mM) and 4-isopropylphenyl hydrazine hydrochloride (8.90 g, 47.6 mM) in ethanol (72 mL) was added triethylamine (7.6 mL, 54.5 mM) to give a brown solution. This solution was refluxed for 16 hours, cooled to room temperature, and then added slowly to a mixture of hydrochloric acid (12N, 100 mL) and ice (100 mL) with vigorous stirring whereupon a pink suspension formed. The suspension was filtered, and the collected solids were washed with a cold solution made by mixing methanol (100 mL), hydrochloric acid (100 mL, 12N) and ice (100 g) to give the 4-isopropylphenyl hydrazine salt of the title compound as a purple powder (1.80 g). This material was refluxed in glacial acetic acid (15 mL) for 3 hours to give a tan suspension. The suspension was cooled to room temperature and filtered. The collected solids were washed with glacial acetic acid (10 mL) and ether to give the title compound (1.125 g, 43%) as a tan powder, mp 367-369° C.: MS(CI): 382 (M+H).

Workup

  1. customto give a brown solution
  2. temperatureThis solution was refluxed for 16 hours
  3. customformed
  4. filtrationThe suspension was filtered
  5. washthe collected solids were washed with a cold solution
  6. additionby mixing methanol (100 mL), hydrochloric acid (100 mL, 12N) and ice (100 g)

Sources & evidence

ORD record
ord-f1d8ffae23af447baff01a6e556606ef
Source dataset
uspto-grants-2001_05
Patent number
US06232313B1

Reaction notes

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