Ammonium Chloride → 2-(6-Amino-7-methoxy-quinolin-2-ylamino)-ethanol

HRID 1773564Notes

Reaction equation

HRID 1773564 reaction equation
[CH3:1][O:2][C:3]1[CH:12]=[C:11]2[C:6]([CH:7]=[CH:8][C:9]([NH:13][CH2:14][CH2:15][OH:16])=[N:10]2)=[CH:5][C:4]=1[N+:17]([O-])=O.[Cl-].[NH4+]>C(O)C.CN(C)C=O.[Fe]>[NH2:17][C:4]1[CH:5]=[C:6]2[C:11](=[CH:12][C:3]=1[O:2][CH3:1])[N:10]=[C:9]([NH:13][CH2:14][CH2:15][OH:16])[CH:8]=[CH:7]2

Participants

6

Reactant 2

HCID 25517Ammonium ChlorideHCID 580563092-(7-Methoxy-6-nitro-quinolin-2-ylamino)-ethanol

Product 1

HCID 580562842-(6-Amino-7-methoxy-quinolin-2-ylamino)-ethanolYield 95.9%

Reagents, catalysts & solvents 3

HCID 23925IronCatalystHCID 702EthanolSolventHCID 6228DimethylformamideSolvent

Procedure

A mixture of 2-(7-methoxy-6-nitro-quinolin-2-ylamino)-ethanol (0.5 g, 1.90 mmol), iron powder (0.32 g, 5.70 mmol) and ammonium chloride (0.32 g, 5.70 mmol) in a mixture of ethanol and water (3/1, 16 mL) was heated at reflux for 2 hours. The reaction mixture was then filtered through a CELITE™ pad, the filtrate was evaporated under reduced pressure and the residue was triturated ten times with a mixture of dichloromethane and methanol (9/1, 50 mL). The residue was concentrated under reduced pressure to afford 0.425 g of 2-(6-amino-7-methoxy-quinolin-2-ylamino)-ethanol as a brown solid.

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 2 hours
  3. filtrationThe reaction mixture was then filtered through a CELITE™ pad
  4. customthe filtrate was evaporated under reduced pressure
  5. customthe residue was triturated ten times
  6. additionwith a mixture of dichloromethane and methanol (9/1, 50 mL)
  7. concentrationThe residue was concentrated under reduced pressure

Sources & evidence

ORD record
ord-abfa5156c09c402da09107670c6a44b7
Source dataset
uspto-grants-2016_02
Patent number
US09255110B2

Reaction notes

Loading…