Lithium iodide → HCID 70047337, compound

HRID 1253295Notes

Reaction equation

HRID 1253295 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[NH:11][C:10](=[O:12])[C:9]([OH:17])(C(OC)=O)[CH:8]([C:18]3[CH:23]=[CH:22][C:21]([O:24][CH3:25])=[CH:20][CH:19]=3)[CH2:7][C:6]=2[CH:26]=1.[I-].[Li+]>N1C=CC=CC=1>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[NH:11][C:10](=[O:12])[C@@H:9]([OH:17])[C@@H:8]([C:18]3[CH:23]=[CH:22][C:21]([O:24][CH3:25])=[CH:20][CH:19]=3)[CH2:7][C:6]=2[CH:26]=1

Participants

4

Reactant 2

HCID 66321Lithium iodideHCID 14156204HCID 14156204, compound

Product 1

HCID 70047337HCID 70047337, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A solution of 7-chloro-1,3,4,5-tetrahydro3-hydroxy-3-(methoxycarbonyl)-4-(4-methoxyphenyl)-2H-1-benzazepin-2-one (0.5 g, 1.33 mmole) and lithium iodide (0.178 g, 1.33 mmole) in dry pyridine (20 ml) was refluxed under argon until complete conversion to product by TLC. The reaction was cooled to room temperature and concentrated in vacuo. The residue was dissolved in chloroform and extracted twice with 1N hydrochloric acid, once with saturated sodium chloride, and dried over magnesium sulfate. The solvent was removed in vacuo and the residue was triturated with ether to yield 0.22 g of the cis product.

Workup

  1. concentrationconcentrated in vacuo
  2. dissolutionThe residue was dissolved in chloroform
  3. extractionextracted twice with 1N hydrochloric acid, once with saturated sodium chloride
  4. dry with materialdried over magnesium sulfate
  5. customThe solvent was removed in vacuo
  6. customthe residue was triturated with ether
  7. customto yield 0.22 g of the cis product

Sources & evidence

ORD record
ord-d7d601513c0345a1a47f33d516c3c6d8
Source dataset
uspto-grants-1988_05
Patent number
US04748239

Reaction notes

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