Hydrochloric Acid → HCID 178524712, compound

HRID 402613Notes

Reaction equation

HRID 402613 reaction equation
[NH:1]1[C:5]2=[N:6][CH:7]=[CH:8][CH:9]=[C:4]2[C:3]([CH:10]=[C:11]2[O:15][C:14]([NH:16][C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)=[C:13]([C:23]([O:25]CC)=[O:24])[C:12]2=[O:28])=[CH:2]1.[OH-].[K+].Cl>C(O)C.O1CCCC1>[NH:1]1[C:5]2=[N:6][CH:7]=[CH:8][CH:9]=[C:4]2[C:3]([CH:10]=[C:11]2[O:15][C:14]([NH:16][C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)=[C:13]([C:23]([OH:25])=[O:24])[C:12]2=[O:28])=[CH:2]1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 14797Potassium HydroxideHCID 178469515HCID 178469515, compound

Product 1

HCID 178524712HCID 178524712, compoundYield 26.6%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of the compound (0.050 g, 0.13 mmol) of Example 1 in ethanol (1.0 mL), 50% potassium hydroxide solution (0.5 mL, 0.13 mmol) was added at ambient temperature. The mixture was refluxed for 1 h. Cooled to ambient temperature, the precipitate was collected by filtration, washed with ethanol. The crude material was dissolved in water (0.5 mL) and tetrahydrofuran (0.5 mL), then 2M hydrochloric acid (0.023 mL, 0.046 mmol) was added and the mixture was stirred for 30 min. The precipitate was collected by filtration, washed with water and diethyl ether then dried to afford the titled compound (0.012 g, y. 26%).

Workup

  1. temperatureThe mixture was refluxed for 1 h
  2. filtrationthe precipitate was collected by filtration
  3. washwashed with ethanol
  4. dissolutionThe crude material was dissolved in water (0.5 mL)
  5. filtrationThe precipitate was collected by filtration
  6. washwashed with water and diethyl ether
  7. customthen dried

Sources & evidence

ORD record
ord-254dd075ed3643a0b467c16b152c5d3a
Source dataset
uspto-grants-2014_06
Patent number
US08742113B2

Reaction notes

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