Hydrochloric Acid → HCID 22310837, compound

HRID 2305582Notes

Reaction equation

HRID 2305582 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-5c4b76848c6f44b2aac02f27990e6c95
Source dataset
uspto-grants-2002_08
Patent number
US06441004B1

Reaction notes

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