Hydrochloric Acid → HCID 131714806, compound

HRID 364168Notes

Reaction equation

HRID 364168 reaction equation
[CH2:1]([N:3]([CH2:45][CH3:46])[CH2:4][CH2:5][N:6]1[C:14]2[CH:13]=[CH:12][C:11]([NH:15][C:16](=[O:36])[CH2:17][N:18]([CH2:26][CH2:27][O:28]CC3C=CC=CC=3)CC3C=CC=CC=3)=[C:10]3[O:37][C:38]4[CH:43]=[CH:42][C:41]([OH:44])=[CH:40][C:39]=4[C:8]([C:9]=23)=[N:7]1)[CH3:2].[H][H].[ClH:49].O>C(O)(=O)C.[OH-].[OH-].[Pd+2]>[ClH:49].[CH2:45]([N:3]([CH2:1][CH3:2])[CH2:4][CH2:5][N:6]1[C:14]2[CH:13]=[CH:12][C:11]([NH:15][C:16](=[O:36])[CH2:17][NH:18][CH2:26][CH2:27][OH:28])=[C:10]3[O:37][C:38]4[CH:43]=[CH:42][C:41]([OH:44])=[CH:40][C:39]=4[C:8]([C:9]=23)=[N:7]1)[CH3:46]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 13689017HCID 13689017, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 131714806HCID 131714806, compound

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 176Acetic AcidSolvent

Procedure

A mixture of 1.3 g of the above acetamide and 0.10 g of 20% palladium hydroxide on carbon in 50 ml of glacial acetic acid stirred under hydrogen at atmospheric pressure until the hydrogen uptake measured 100 ml. The reaction mixture was filtered and coevaporated several times with methanol. The residue was dissolved in methanol and acidified with a solution of hydrogen chloride in 2-propanol. Further dilution with 2-propanol and cooling caused precipitation of a crystalline solid. The solid was isolated and dried to give 0.976 g of the product as a yellow crystalline solid with 2.5 equivalents of hydrogen chloride and 1.5 equivalents of water, mp 285° C. with decomposition.

Workup

  1. filtrationThe reaction mixture was filtered
  2. dissolutionThe residue was dissolved in methanol
  3. temperatureFurther dilution with 2-propanol and cooling
  4. customprecipitation of a crystalline solid
  5. customThe solid was isolated
  6. customdried

Sources & evidence

ORD record
ord-788ca1ce0de8413e8bd24d5e6350fbaf
Source dataset
uspto-grants-1986_08
Patent number
US04604390

Reaction notes

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