Hydrochloric Acid → HCID 22310837, compound

HRID 967099Notes

Reaction equation

HRID 967099 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:23]=[CH:24][C:25]=1[Cl:26])[CH2:5][N:6]1[C:14]2[C:9](=[CH:10][C:11]([NH:15][C:16](=[O:18])[CH3:17])=[CH:12][CH:13]=2)[CH:8]=[C:7]1[C:19]([O:21]C)=[O:20].[I-].[Li+].Cl>N1C=CC=CC=1>[Cl:1][C:2]1[CH:3]=[C:4]([CH:23]=[CH:24][C:25]=1[Cl:26])[CH2:5][N:6]1[C:14]2[C:9](=[CH:10][C:11]([NH:15][C:16](=[O:18])[CH3:17])=[CH:12][CH:13]=2)[CH:8]=[C:7]1[C:19]([OH:21])=[O:20]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 66321Lithium iodideHCID 22310834HCID 22310834, compound

Product 1

HCID 22310837HCID 22310837, compoundYield 22.4%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

Methyl N-(3,4-Dichlorobenzyl)-5-acetylaminoindole-2-carboxylate (88 mg) and lithium iodide (300 mg) were dissolved in pyridine and heated at reflux for 8 hours, then cooled to room temperature and poured into 2M HCl and extracted with diethyl ether. Combined organic extracts were dried (MgSO4) and concentrated in vacuo to give an oil which was purified by column chromatography using DCM-2% methanol as eluent to give the desired end product as a white solid (19 mg, 22%), mp 245-246°; NMR δ (CD3SOCD3) 2.02 (s, 3H), 5.82 (s, 2H), 6.90 (d, 1H), 7.20-7.55 (m, 5H), 8.02 (s, 1H), 9.83 (s, 1H); M/z (+) 377 (MH+), 278.

Workup

  1. temperatureheated
  2. temperatureat reflux for 8 hours
  3. extractionextracted with diethyl ether
  4. dry with materialCombined organic extracts were dried (MgSO4)
  5. concentrationconcentrated in vacuo
  6. customto give an oil which
  7. customwas purified by column chromatography

Sources & evidence

ORD record
ord-3ba03778e3c7424e94cc40a914e612b6
Source dataset
uspto-grants-2005_10
Patent number
US06953809B2

Reaction notes

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