Potassium tert-butoxide → HCID 54455005, compound

HRID 1195753Notes

Reaction equation

HRID 1195753 reaction equation
[NH2:1][C:2]1[C:3]2[C:8]([N:9]=[C:10]3[C:15]=1[CH:14]([O:16][CH2:17][C:18]([O:20]C)=O)[CH2:13][CH2:12][CH2:11]3)=[CH:7][CH:6]=[CH:5][CH:4]=2.CC(C)([O-])C.[K+]>O1CCCC1>[NH:1]1[C:2]2=[C:3]3[C:8](=[N:9][C:10]4[CH2:11][CH2:12][CH2:13][CH:14]([C:15]=42)[O:16][CH2:17][C:18]1=[O:20])[CH:7]=[CH:6][CH:5]=[CH:4]3

Participants

4

Reactant 2

HCID 23665647Potassium tert-butoxideHCID 54251529HCID 54251529, compound

Product 1

HCID 54455005HCID 54455005, compoundYield 39%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of methyl [(9-amino-1,2,3,4-tetrahydroacridin-1-yl)oxy]acetate (13.7 g) in tetrahydrofuran (200 ml) was added potassium t-butoxide (6.7 g). The reaction mixture was stirred at ambient temperature for 2.5 hrs and evaporated. The residue was stirred in dilute potassium carbonate solution/ethyl ether. The precipitate was collected and dried. A 3.5 g sample was recrystallized twice from methanol/water, passed through a column of basic alumina (5% methanol/ethyl acetate) and recrystallized from methanol to give 1.37 g (39%) of product, mp 173°-175° C.

Workup

  1. customevaporated
  2. stirringThe residue was stirred in dilute potassium carbonate solution/ethyl ether
  3. customThe precipitate was collected
  4. customdried
  5. customA 3.5 g sample was recrystallized twice from methanol/water
  6. customrecrystallized from methanol

Sources & evidence

ORD record
ord-c4117e41c623455ea27ddc8eb6aea1b1
Source dataset
uspto-grants-1992_05
Patent number
US05112829

Reaction notes

Loading…