Hydrochloric Acid → HCID 21460690, compound

HRID 2396352Notes

Reaction equation

HRID 2396352 reaction equation
[CH2:1]([N:10]([CH2:27][C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1)[C:11]1[C:19]2[C:14](=[CH:15][C:16]([Cl:21])=[CH:17][C:18]=2[Cl:20])[NH:13][C:12]=1[C:22]([O:24]CC)=[O:23])[C:2]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1)=[O:3].O.[OH-].[Li+].Cl>O1CCCC1.O>[CH2:1]([N:10]([CH2:27][C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1)[C:11]1[C:19]2[C:14](=[CH:15][C:16]([Cl:21])=[CH:17][C:18]=2[Cl:20])[NH:13][C:12]=1[C:22]([OH:24])=[O:23])[C:2]([C:4]1[CH:5]=[CH:6][CH:7]=[CH:8][CH:9]=1)=[O:3]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 168937Lithium hydroxide, monohydrateHCID 21460764HCID 21460764, compound

Product 1

HCID 21460690HCID 21460690, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

Dissolve 3-[(phenacyl)benzylamino]-2-carbethoxy-4,6-dichloroindole (0.5 g, 1.07 mmol) in tetrahydrofuran (10 mL) and water (10 mL). Add lithium hydroxide monohydrate (0.16 g, 3.74 mmol) and stir for 24 hours. Heat at reflux for 6 hours and pour into 1N hydrochloric acid (100 mL). Extract into ethyl acetate, dry (MgSO4) and evaporate the solvent in vacuo. Recrystallize (ethyl acetate/hexane) to give the title compound; mp 266°-7° C.

Workup

  1. temperatureHeat
  2. temperatureat reflux for 6 hours
  3. extractionExtract into ethyl acetate
  4. dry with materialdry (MgSO4)
  5. customevaporate the solvent in vacuo
  6. customRecrystallize (ethyl acetate/hexane)

Sources & evidence

ORD record
ord-4ab2829c37c749fc8d9ce5f56dd89f15
Source dataset
uspto-grants-1996_02
Patent number
US05491153

Reaction notes

Loading…