Lithium iodide → HCID 70047337, compound

HRID 1253297Notes

Reaction equation

HRID 1253297 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-tetrahydro-3-hydroxy-3-(methoxycarbonyl)-4-(4-methoxyphenyl)-2H-1-benzazepin-2-one (16.4 g, 43.7 mmole) and lithium iodide (23.7 g, 174.6 mmole) in 290 ml of pyridine containing 1% water was refluxed under argon until complete conversion to product by TLC (ca. 1.5 hours). The reaction was cooled to room temperature and concentrated in vacuo. The residue was dissolved in ethyl acetate and extracted with 1N hydrochloric acid, saturated sodium bicarbonate and saturated sodium chloride. The solution was dried over magnesium sulfate and concentrated. The residue was recrystallized from ethyl acetate to afford 6.8 g of pure cis product.

Workup

  1. concentrationconcentrated in vacuo
  2. dissolutionThe residue was dissolved in ethyl acetate
  3. extractionextracted with 1N hydrochloric acid, saturated sodium bicarbonate and saturated sodium chloride
  4. dry with materialThe solution was dried over magnesium sulfate
  5. concentrationconcentrated
  6. customThe residue was recrystallized from ethyl acetate
  7. customto afford 6.8 g of pure cis product

Sources & evidence

ORD record
ord-4ecfc82b23b34195922e71fd44e703c5
Source dataset
uspto-grants-1988_05
Patent number
US04748239

Reaction notes

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