Sodium dithionate → 3-[(3-Amino-7-bromoquinolin-4-yl)amino]propan-1-ol

HRID 1992605Notes

Reaction equation

HRID 1992605 reaction equation
S(S([O-])(=O)=O)([O-])(=O)=O.[Na+].[Na+].[Br:11][C:12]1[CH:21]=[C:20]2[C:15]([C:16]([NH:25][CH2:26][CH2:27][CH2:28][OH:29])=[C:17]([N+:22]([O-])=O)[CH:18]=[N:19]2)=[CH:14][CH:13]=1>O.C(O)C>[NH2:22][C:17]1[CH:18]=[N:19][C:20]2[C:15]([C:16]=1[NH:25][CH2:26][CH2:27][CH2:28][OH:29])=[CH:14][CH:13]=[C:12]([Br:11])[CH:21]=2

Participants

5

Reactant 2

HCID 146045Sodium dithionateHCID 666198783-[(7-Bromo-3-nitroquinolin-4-yl)amino]propan-1-ol

Product 1

HCID 685364133-[(3-Amino-7-bromoquinolin-4-yl)amino]propan-1-olYield 77.7%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

A solution of sodium dithionate (27.5 g, 158 mmol) in water (60 mL) was added to a solution of 3-[(7-bromo-3-nitroquinolin-4-yl)amino]propan-1-ol (10.3 g, 31.6 mmol) in ethanol (175 mL), and the mixture was stirred vigorously for four hours at ambient temperature. The solvent was removed under reduced pressure, and the residue was partitioned between dichloromethane/chloroform/methanol (500 mL) and saturated aqueous sodium bicarbonate (200 mL). The aqueous layer was separated and extracted with chloroform (5×200 mL), and the combined organic fractions were dried over sodium sulfate, filtered, and concentrated under reduced pressure to provide 7.27 g of 3-[(3-amino-7-bromoquinolin-4-yl)amino]propan-1-ol.

Workup

  1. customThe solvent was removed under reduced pressure
  2. customthe residue was partitioned between dichloromethane/chloroform/methanol (500 mL) and saturated aqueous sodium bicarbonate (200 mL)
  3. customThe aqueous layer was separated
  4. extractionextracted with chloroform (5×200 mL)
  5. dry with materialthe combined organic fractions were dried over sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-ea760dfa0a2741b99e5887a61329acb8
Source dataset
uspto-grants-2010_01
Patent number
US07648997B2

Reaction notes

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