Hydrochloric Acid → HCID 71255256, compound

HRID 540334Notes

Reaction equation

HRID 540334 reaction equation
[CH2:1]1[C:7]2[CH:8]=[CH:9][CH:10]=[CH:11][C:6]=2[CH2:5][CH2:4][CH2:3][N:2]1[C:12]1[CH:21]=[C:20]([CH2:22][CH2:23][C:24]([O:26]C)=[O:25])[C:19]2[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=2)[N:13]=1.[OH-].[Na+].Cl>CO>[CH2:1]1[C:7]2[CH:8]=[CH:9][CH:10]=[CH:11][C:6]=2[CH2:5][CH2:4][CH2:3][N:2]1[C:12]1[CH:21]=[C:20]([CH2:22][CH2:23][C:24]([OH:26])=[O:25])[C:19]2[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=2)[N:13]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 71255205HCID 71255205, compound

Product 1

HCID 71255256HCID 71255256, compoundYield 82%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of methyl 3-[2-(1,3,4,5-tetrahydro-2H-2-benzazepin-2-yl)quinolin-4-yl]propanoate (1.4 g, 3.89 mmol) in methanol (10 mL) was added an aqueous solution of sodium hydroxide (4 N, 16 mL) and the resulting mixture was stirred at room temperature for 4 hours. The reaction was acidified to pH 4 with 5 N hydrochloric acid, and then extracted with ethyl acetate (10 mL×3). The organic layer was dried over sodium sulfate and concentrated in vacuo to give a residue which was purified by flash column chromatography to afford 1.1 g of product as a white solid (yield was 82%). MS obsd. (ESI+) [(M+H)+] 347.

Workup

  1. extractionextracted with ethyl acetate (10 mL×3)
  2. dry with materialThe organic layer was dried over sodium sulfate
  3. concentrationconcentrated in vacuo
  4. customto give a residue which
  5. customwas purified by flash column chromatography

Sources & evidence

ORD record
ord-a7033c3a9bc9463ba19af6a8fe3c418c
Source dataset
uspto-grants-2014_10
Patent number
US08871756B2

Reaction notes

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