(Benzyloxy)methyl-8-methyl-2,3-dihydro[1,4]dioxino[2,3-f]quinoline → [8-Methyl-2,3-Dihydro[1,4]Dioxino[2,3-f]Quinolin-2-yl]Methanol

HRID 2120995Notes

Reaction equation

HRID 2120995 reaction equation
C([O:8][CH2:9][CH:10]1[O:24][C:14]2=[C:15]3[C:20](=[CH:21][CH:22]=[C:13]2[O:12][CH2:11]1)[N:19]=[C:18]([CH3:23])[CH:17]=[CH:16]3)C1C=CC=CC=1>C(Cl)Cl>[CH3:23][C:18]1[CH:17]=[CH:16][C:15]2[C:20](=[CH:21][CH:22]=[C:13]3[O:12][CH2:11][CH:10]([CH2:9][OH:8])[O:24][C:14]3=2)[N:19]=1

Participants

3

Reactant 1

HCID 22172756(Benzyloxy)methyl-8-methyl-2,3-dihydro[1,4]dioxino[2,3-f]quinoline

Product 1

HCID 21892068[8-Methyl-2,3-Dihydro[1,4]Dioxino[2,3-f]Quinolin-2-yl]MethanolYield 69%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 2[(benzyloxy)methyl-8-methyl-2,3-dihydro[1,4]dioxino [2,3-f]quinoline (0.30 g, 0.94 mmol) in CH2Cl2 (8 mL) being cooled in an ice-bath, FeCl3 (0.77 g, 4.7 mmol) was added. After 1 h, the ice-bath was removed and the reaction mixture was stirred for another 4 h. CH2Cl2 (30 mL) and 1N NaOH (25 mL) were added to result in a suspension which was then filtered. The filtered solid was washed with CH3OH (50 mL). The combined organic layers were concentrated in vacuo. Purification on SiO2, eluted with (10:1) CHCl3:iPrOH gave 0.15 g (68%) of the title compound as an off-white solid.

Workup

  1. customthe ice-bath was removed
  2. additionCH2Cl2 (30 mL) and 1N NaOH (25 mL) were added
  3. customto result in a suspension which
  4. filtrationwas then filtered
  5. washThe filtered solid was washed with CH3OH (50 mL)
  6. concentrationThe combined organic layers were concentrated in vacuo
  7. customPurification on SiO2
  8. washeluted with (10:1) CHCl3

Sources & evidence

ORD record
ord-d86a2703d535424b89330d980df843f4
Source dataset
uspto-grants-2004_02
Patent number
US06693197B2

Reaction notes

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