Sodium Hydroxide → 4-Aminoquinoline

HRID 2187356Notes

Reaction equation

HRID 2187356 reaction equation
C(OC(=O)[NH:7][C:8]1[C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[N:11]=[CH:10][CH:9]=1)(C)(C)C.[OH-].[Na+]>Cl.O>[NH2:7][C:8]1[C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[N:11]=[CH:10][CH:9]=1

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 70701225tert-Butyl quinolin-4-ylcarbamate

Product 1

HCID 684764-AminoquinolineYield 87.7%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 962WaterSolvent

Procedure

A solution of quinolin-4-yl carbamic acid tert butyl ester (16.8 g) in 5N HCl (200 ml) was boiled for 5 h. The reaction mixture was diluted with water made basic with sodium hydroxide and washed with dichloromethane. The aqueous phase was separated and evaporated to dryness at reduced pressure. The residue was dissolved in propan-1-ol, insoluble material separated by filtration and the filtrate evaporated to dryness. The residue was dissolved in dichloromethane/ethyl acetate, filtered to remove insoluble inorganic salts and solvent removed at reduced pressure to give 4-aminoquinoline (8.7 g).

Workup

  1. washwashed with dichloromethane
  2. customThe aqueous phase was separated
  3. customevaporated to dryness at reduced pressure
  4. dissolutionThe residue was dissolved in propan-1-ol
  5. custominsoluble material separated by filtration
  6. customthe filtrate evaporated to dryness
  7. dissolutionThe residue was dissolved in dichloromethane/ethyl acetate
  8. filtrationfiltered
  9. customto remove insoluble inorganic salts and solvent
  10. customremoved at reduced pressure

Sources & evidence

ORD record
ord-4062990224804a2986a994f99ce48f98
Source dataset
uspto-grants-2002_06
Patent number
US06410529B1

Reaction notes

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