Water → HCID 69047243, compound

HRID 2196585Notes

Reaction equation

HRID 2196585 reaction equation
[N:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[C:4]([CH2:11][N:12]2[CH2:21][CH2:20][C:19]3[C:18]([C:22]([O:24]C)=[O:23])=[CH:17][CH:16]=[CH:15][C:14]=3[CH2:13]2)=[CH:3][CH:2]=1.O.[OH-].[Na+]>O1CCOCC1>[N:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[C:4]([CH2:11][N:12]2[CH2:21][CH2:20][C:19]3[C:18]([C:22]([OH:24])=[O:23])=[CH:17][CH:16]=[CH:15][C:14]=3[CH2:13]2)=[CH:3][CH:2]=1

Participants

5

Reactant 3

HCID 962WaterHCID 14798Sodium HydroxideHCID 69047732HCID 69047732, compound

Product 1

HCID 69047243HCID 69047243, compoundYield 92.2%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

Methyl 2-(quinolin-4-ylmethyl)-1,2,3,4-tetrahydroisoquinoline-5-carboxylate (1.2 g, 3.61 mmol) was dissolved in dioxane (15 mL) and water (5 mL) then added a solution of 2N aqueous sodium hydroxide (1.90 mL, 3.80 mmol). The reaction mixture was stirred at room temperature for 2 days then concentrated under vacuum to remove the dioxane. The remaining aqueous solution was diluted with water then added 1N aqueous hydrochloric acid (3.8 mL) to bring the mixture to pH 7. A precipitate formed which was collected on a glass frit, washing with minimal water then dichloromethane. The solid was dried under high vacuum to afford 1.06 g of 2-(quinolin-4-ylmethyl)-1,2,3,4-tetrahydroisoquinoline-5-carboxylic acid as a white solid. MS (ESI, pos. ion) m/z: 319.1 (M+1).

Workup

  1. concentrationthen concentrated under vacuum
  2. customto remove the dioxane
  3. additionThe remaining aqueous solution was diluted with water
  4. additionthen added 1N aqueous hydrochloric acid (3.8 mL)
  5. customA precipitate formed which
  6. customwas collected on a glass frit
  7. washwashing with minimal water
  8. customThe solid was dried under high vacuum

Sources & evidence

ORD record
ord-4d2b6d03835b42d8aabeb324039d9fd3
Source dataset
uspto-grants-2012_12
Patent number
US08338455B2

Reaction notes

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