Hydrochloric Acid → HCID 9911732, compound

HRID 2396355Notes

Reaction equation

[CH2:1]([C:8]1[CH:33]=[CH:32][CH:31]=[CH:30][C:9]=1[C:10](=[O:29])[CH2:11][NH:12][C:13]1[C:21]2[C:16](=[CH:17][C:18]([Cl:23])=[CH:19][C:20]=2[Cl:22])[NH:15][C:14]=1[C:24]([O:26]CC)=[O:25])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.O.[OH-].[Li+].Cl>O1CCCC1.O.C(OCC)(=O)C>[CH2:1]([C:8]1[CH:33]=[CH:32][CH:31]=[CH:30][C:9]=1[C:10](=[O:29])[CH2:11][NH:12][C:13]1[C:21]2[C:16](=[CH:17][C:18]([Cl:23])=[CH:19][C:20]=2[Cl:22])[NH:15][C:14]=1[C:24]([OH:26])=[O:25])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

Conditions

Temperature: 40 °C

Procedure

Dissolve 3-[(2-benzylphenacyl)amino]-2-carbethoxy-4,6-dichloroindole (100 mg, 0.214 mmol) in tetrahydrofuran (7 mL) and water (7 mL). Add lithium hydroxide monohydrate (25.2 mg, 6 mmol) and stir overnight. Stir at 40° C. for 2 hours, dilute with water (10 mL) and ethyl acetate (25mL). Acidify with 1N hydrochloric acid while stirring. Separate the organicphase, dry (MgSO4) and evaporate the solvent in vacuo. Recrystallize (ether/hexane) to give the title compound (89 mg, 95%); mp 234°-235° C.

Workup

customSeparate the organicphase,
dry with materialdry (MgSO4)
customevaporate the solvent in vacuo
customRecrystallize (ether/hexane)

Sources & evidence

ORD record: ord-3de14c8f3ca74117b18d24879b5d2689
Source dataset: uspto-grants-1996_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05491153

Reaction notes

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