Hydrochloric Acid → HCID 2801547, compound

HRID 1632188Notes

Reaction equation

HRID 1632188 reaction equation
C([NH:4][C:5]1[CH:20]=[CH:19][C:8]2[C:9](=[O:18])[CH:10]=[C:11]([C:13]([O:15][CH2:16][CH3:17])=[O:14])[O:12][C:7]=2[C:6]=1[CH2:21][CH2:22][CH3:23])(=O)C.Cl>C(O)C.O>[NH2:4][C:5]1[CH:20]=[CH:19][C:8]2[C:9](=[O:18])[CH:10]=[C:11]([C:13]([O:15][CH2:16][CH3:17])=[O:14])[O:12][C:7]=2[C:6]=1[CH2:21][CH2:22][CH3:23]

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 13101141HCID 13101141, compound

Product 1

HCID 2801547HCID 2801547, compoundYield 55.3%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

A solution of the amide of step (d) (10 g) in ethanol (300 ml), containing concentrated hydrochloric acid (5 ml), was refluxed for 8 hours. The reaction mixture was diluted with water and extracted into ethyl acetate. The extract was washed with water, dried and the solvent was evaporated to leave a dark brown semisolid. This was chromatographed on a silica gel column, using ether as eluant to give 4.8 g of the required product whose structure was confirmed by mass and NMR spectral evidence; mp 84°-87° C.

Workup

  1. temperaturewas refluxed for 8 hours
  2. extractionextracted into ethyl acetate
  3. washThe extract was washed with water
  4. customdried
  5. customthe solvent was evaporated
  6. customto leave a dark brown semisolid
  7. customThis was chromatographed on a silica gel column

Sources & evidence

ORD record
ord-488582ca132242c6a2ff411c78909daa
Source dataset
uspto-grants-1984_10
Patent number
US04474787

Reaction notes

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