Hydrochloric Acid → HCID 9911732, compound

HRID 2082517Notes

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 (25 mL). Acidify with 1N hydrochloric acid while stirring. Separate the organic phase, 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 organic phase
dry with materialdry (MgSO4)
customevaporate the solvent in vacuo
customRecrystallize (ether/hexane)

Sources & evidence

ORD record: ord-1e2e31eb8d604811ba56c941bc0a0178
Source dataset: uspto-grants-1993_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05189054

Reaction notes

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