Hydrochloric Acid → HCID 69947523, compound

HRID 1979031Notes

Reaction equation

HRID 1979031 reaction equation
C([O:3][C:4]([CH:6]1[CH2:11][CH2:10][N:9]([CH2:12][CH2:13][CH2:14][N:15]2[C:21]3[CH:22]=[CH:23][CH:24]=[CH:25][C:20]=3[CH2:19][CH2:18][C:17]3[CH:26]=[CH:27][CH:28]=[CH:29][C:16]2=3)[CH2:8][CH2:7]1)=[O:5])C.[OH-].[Na+].[ClH:32]>C(O)C.O.CO.C(OCC)(=O)C>[ClH:32].[CH:26]1[C:17]2[CH2:18][CH2:19][C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=3[N:15]([CH2:14][CH2:13][CH2:12][N:9]3[CH2:8][CH2:7][CH:6]([C:4]([OH:5])=[O:3])[CH2:11][CH2:10]3)[C:16]=2[CH:29]=[CH:28][CH:27]=1

Participants

8

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 54172756HCID 54172756, compound

Product 1

HCID 69947523HCID 69947523, compoundYield 88%

Reagents, catalysts & solvents 4

HCID 702EthanolSolventHCID 887MethanolSolventHCID 962WaterSolvent2×HCID 8857Ethyl AcetateSolvent2×

Procedure

The above ester (1.01 g, 2.57 mmol) was dissolved in ethanol (10 ml), and a solution of sodium hydroxide (0.59 g, 14.8 mmol) in water (1.5 ml) was added. The resulting mixture was stirred at room temperature for 3.5 h. A mixture of water (20 ml) and concentrated hydrochloric acid (3.0 ml) was added, and the aqueous phase was extracted with dichloromethane (3×15 ml). The combined organic extracts were washed with brine (20 ml) and dried (MgSO4). Evaporation of the solvent gave a foam, which was redissolved in a mixture of methanol (1.0 ml) and ethyl acetate (5.0 ml). Concentration in vacuo afforded a solid, which was suspended in ethyl acetate (15 ml), heated at reflux temperature for 1 minute and allowed to cool to room temperature. The solid was filtered off and dried to give 0.9 g (88%) of the title compound as a powder.

Workup

  1. additionwas added
  2. extractionthe aqueous phase was extracted with dichloromethane (3×15 ml)
  3. washThe combined organic extracts were washed with brine (20 ml)
  4. dry with materialdried (MgSO4)
  5. customEvaporation of the solvent
  6. customgave a foam, which
  7. concentrationConcentration in vacuo
  8. customafforded a solid, which
  9. temperatureheated
  10. temperatureat reflux temperature for 1 minute
  11. temperatureto cool to room temperature
  12. filtrationThe solid was filtered off
  13. customdried

Sources & evidence

ORD record
ord-150bc0a506b949cb8dc62da32a45fbfb
Source dataset
uspto-grants-2001_05
Patent number
US06239148B1

Reaction notes

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