Water → HCID 69047155, compound

HRID 2196583Notes

Reaction equation

HRID 2196583 reaction equation
[N:1]1[CH:6]=[CH:5][C:4]([CH2:7][N:8]2[CH2:17][CH2:16][C:15]3[C:14]([C:18]([O:20]C)=[O:19])=[CH:13][CH:12]=[CH:11][C:10]=3[CH2:9]2)=[CH:3][CH:2]=1.O.[OH-].[Na+:24]>O1CCOCC1>[N:1]1[CH:6]=[CH:5][C:4]([CH2:7][N:8]2[CH2:17][CH2:16][C:15]3[C:14]([C:18]([O-:20])=[O:19])=[CH:13][CH:12]=[CH:11][C:10]=3[CH2:9]2)=[CH:3][CH:2]=1.[Na+:24]

Participants

5

Reactant 3

HCID 962WaterHCID 14798Sodium HydroxideHCID 69046637HCID 69046637, compound

Product 1

HCID 69047155HCID 69047155, compoundYield 106.6%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

Methyl 2-(pyridine-4-ylmethyl)-1,2,3,4-tetrahydroisoquinoline-5-carboxylate (1.14 g, 4.04 mmol) was dissolved in dioxane (15 mL) and water (5 mL) then added a solution of 2N aqueous sodium hydroxide (2.22 mL, 4.45 mmol). The reaction mixture was stirred at room temperature for 2 days then concentrated under vacuum. The remaining oil was azeotroped with toluene and dried under high vacuum to afford 1.25 g of sodium 2-(pyridin-4-ylmethyl)-1,2,3,4-tetrahydroisoquinoline-5-carboxylate as a pale yellow oil/foam. MS (ESI, pos. ion) m/z: 269.0 (M+1).

Workup

  1. concentrationthen concentrated under vacuum
  2. customThe remaining oil was azeotroped with toluene
  3. customdried under high vacuum

Sources & evidence

ORD record
ord-5d82d431898f4a6c8f74c3f0a6076501
Source dataset
uspto-grants-2012_12
Patent number
US08338455B2

Reaction notes

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