Sodium Hydroxide → HCID 14685752, compound

HRID 1088805Notes

Reaction equation

HRID 1088805 reaction equation
O=C1[O:7][CH2:6][C:5]2[CH:8]=[CH:9][CH:10]=[C:11]3[CH:12]([N:15]([CH3:19])[CH2:16][CH:17]=[CH2:18])[CH2:13][CH2:14][N:3]1[C:4]=23.[OH-].[Na+]>CO>[CH3:19][N:15]([CH:12]1[C:11]2[C:4](=[C:5]([CH2:6][OH:7])[CH:8]=[CH:9][CH:10]=2)[NH:3][CH2:14][CH2:13]1)[CH2:16][CH:17]=[CH2:18]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 14685751HCID 14685751, compound

Product 1

HCID 14685752HCID 14685752, compoundYield 91.2%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 6,7-dihydro-3-oxo-7-(N-methyl-N-allylamino)-1H,3H,5H-pyrido[3,2,1-ij][3,1]benzoxazine (5.89 g) in methanol (80 ml) was added 15% aqueous solution of sodium hydroxide (20 ml) and the mixture was refluxed for 6 hours. After distilling off methanol and extracting with dichloromethane, the extract was dried over anhydrous magnesium sulfate. The solvent was distilled off to give 4-(N-methyl-N-allylamino)-8-hydroxymethyl-1,2,3,4-tetrahydroquinoline (4.83 g).

Workup

  1. temperaturethe mixture was refluxed for 6 hours
  2. distillationAfter distilling off methanol
  3. extractionextracting with dichloromethane
  4. dry with materialthe extract was dried over anhydrous magnesium sulfate
  5. distillationThe solvent was distilled off

Sources & evidence

ORD record
ord-326edb2efc114f51bd093489be4da1d0
Source dataset
uspto-grants-1990_10
Patent number
US04963566

Reaction notes

Loading…