Lithium hydroxide, monohydrate → HCID 21460775, compound

HRID 2082483Notes

Reaction equation

HRID 2082483 reaction equation
[CH2:1]([NH:10][C:11]1[C:19]2[C:14](=[CH:15][C:16]([Cl:20])=[CH:17][CH:18]=2)[NH:13][C:12]=1[C:21]([O:23]C)=[O:22])[C:2]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1)=[O:3].O.[OH-].[Li+]>O1CCCC1.O.C(OCC)(=O)C.O>[CH2:1]([NH:10][C:11]1[C:19]2[C:14](=[CH:15][C:16]([Cl:20])=[CH:17][CH:18]=2)[NH:13][C:12]=1[C:21]([OH:23])=[O:22])[C:2]([C:4]1[CH:5]=[CH:6][CH:7]=[CH:8][CH:9]=1)=[O:3]

Participants

5

Reactant 2

HCID 168937Lithium hydroxide, monohydrateHCID 21460734HCID 21460734, compound

Product 1

HCID 21460775HCID 21460775, compound

Reagents, catalysts & solvents 2

HCID 21881883Oxolane--water (1/1)SolventHCID 22728543Water ethylacetateSolvent

Conditions

Temperature
60 °C

Procedure

Dissolve 3-[(phenacyl)amino]-2-carbmethoxy-6-chloroindole (480 mg, 1.46 mmol) in tetrahydrofuran/water (20 mL, 1/1). Add lithium hydroxide monohydrate (316 mg, 2.92 mmol). Seal the flask and warm to 60° C. for 3 hours. Dilute with ethyl acetate/water (50 mL/50 mL) and separate the organic phase. Acidify the aqueous phase and extract with ethyl acetate. Dry (MgSO4) the combined organic phases and concentrate in vacuo. Precipitate with hexane to give the title compound; first crop (289 mg, 63%) and second crop (74 mg, 16%); mp 205°-210° C. (dec).

Workup

  1. customSeal the flask
  2. customseparate the organic phase
  3. extractionextract with ethyl acetate
  4. dry with materialDry (MgSO4) the combined organic phases
  5. concentrationconcentrate in vacuo

Sources & evidence

ORD record
ord-bcc6ccd70b594d5095e22436ab970ad5
Source dataset
uspto-grants-1993_02
Patent number
US05189054

Reaction notes

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