Hydrochloric Acid → HCID 19348135, compound

HRID 1637284Notes

Reaction equation

HRID 1637284 reaction equation
[NH2:1][CH:2]1[C:12]2[C:13]3[C:5](=[C:6]([C:15]4[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=4[O:21][CH3:22])[NH:7][C:8]=3[C:9](Cl)=[CH:10][CH:11]=2)[CH2:4][CH2:3]1.Cl.C(=O)([O-])[O-].[K+].[K+]>CO.[C].[Pd]>[NH2:1][CH:2]1[C:12]2[C:13]3[C:5](=[C:6]([C:15]4[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=4[O:21][CH3:22])[NH:7][C:8]=3[CH:9]=[CH:10][CH:11]=2)[CH2:4][CH2:3]1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 11430Potassium CarbonateHCID 19348153HCID 19348153, compound

Product 1

HCID 19348135HCID 19348135, compoundYield 72.1%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 887MethanolSolvent

Procedure

A portion (1.45 g) of the compound obtained in Example 183 was dissolved in methanol (50 ml) and 1N hydrochloric acid (50 ml) and to the solution was added 10% palladium-carbon (1.45 g). The mixture was stirred overnight at room temperature under a hydrogen atmosphere. The reaction mixture was neutralized with potassium carbonate, the catalyst and the inorganic salt were filtered off and washed with methylene chloride. The filtrate and the washed liquid were combined, washed with saturated aqueous solution of sodium chloride and dried over anhydrous sodium sulfate. Then, the solvent was distilled off under reduced pressure. The residue was crystallized from ether to yield 0.93 g (72%) of the titled compound as a pale yellow powder.

Workup

  1. filtrationthe catalyst and the inorganic salt were filtered off
  2. washwashed with methylene chloride
  3. washwashed with saturated aqueous solution of sodium chloride
  4. dry with materialdried over anhydrous sodium sulfate
  5. distillationThen, the solvent was distilled off under reduced pressure
  6. customThe residue was crystallized from ether

Sources & evidence

ORD record
ord-fa8b1caf9b874326904bb89147022bb8
Source dataset
uspto-grants-2000_03
Patent number
US06040331

Reaction notes

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