Acetic Anhydride → HCID 22161780, compound

HRID 1088801Notes

Reaction equation

HRID 1088801 reaction equation
[C:1](OC(=O)C)(=[O:3])C.[CH:8]1([NH:11][CH:12]2[C:21]3[C:16](=[C:17]([CH2:22][OH:23])[CH:18]=[CH:19][CH:20]=3)[N:15]([CH2:24][CH3:25])[CH2:14][CH2:13]2)[CH2:10][CH2:9]1.[OH-].[Na+]>C(O)=O>[CH:1]([N:11]([CH:12]1[C:21]2[C:16](=[C:17]([CH2:22][OH:23])[CH:18]=[CH:19][CH:20]=2)[N:15]([CH2:24][CH3:25])[CH2:14][CH2:13]1)[CH:8]1[CH2:9][CH2:10]1)=[O:3]

Participants

5

Reactant 3

HCID 7918Acetic AnhydrideHCID 14798Sodium HydroxideHCID 14685742HCID 14685742, compound

Product 1

HCID 22161780HCID 22161780, compound

Reagents, catalysts & solvents 1

HCID 284Formic AcidSolvent

Procedure

Acetic anhydride (0.5 ml) and formic acid (0.25 ml) were stirred for 1 hour at 60° C, and to this mixture 4-cyclopropylamino-8-hydroxymethyl-1-ethyl-1,2,3,4-tetrahydroquinoline (0.37 g) was added under ice-cooling and the mixture was stirred overnight at room temperature The reaction mixture was adjusted to alkalinic with 30% aqueous solution of sodium hydroxide under ice-cooling, stirred for 0.5 hour, sequentially extracted with dichloromethane. The extract was dried over anhydrous magnesium sulfate The residue, obtained by distilling off the solvent, was purified by silica gel column chromatography [eluent: dichloromethane-methanol (75:1)]to give 4-(N-formyl-N-cyclopropylamino)-8-hydroxymethyl1-ethyl-1,2,3,4-tetrahydroquinoline (0.35 g).

Workup

  1. temperaturecooling
  2. temperaturecooling
  3. stirringstirred for 0.5 hour
  4. extractionsequentially extracted with dichloromethane
  5. dry with materialThe extract was dried over anhydrous magnesium sulfate The residue
  6. customobtained
  7. distillationby distilling off the solvent
  8. customwas purified by silica gel column chromatography [eluent

Sources & evidence

ORD record
ord-b51b39d016ac4cb39fb7cf9935ace80b
Source dataset
uspto-grants-1990_10
Patent number
US04963566

Reaction notes

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