Water → (7-Bromo-3-nitroquinolin-4-yl)-(5-chloropentyl)amine

HRID 9426Notes

Reaction equation

HRID 9426 reaction equation
[Br:1][C:2]1[CH:11]=[C:10]2[C:5]([C:6]([NH:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20]O)=[C:7]([N+:12]([O-:14])=[O:13])[CH:8]=[N:9]2)=[CH:4][CH:3]=1.S(Cl)([Cl:24])=O.C(=O)(O)[O-].[Na+].O>ClCCl>[Br:1][C:2]1[CH:11]=[C:10]2[C:5]([C:6]([NH:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][Cl:24])=[C:7]([N+:12]([O-:14])=[O:13])[CH:8]=[N:9]2)=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 962WaterHCID 24386Thionyl ChlorideHCID 516892Sodium BicarbonateHCID 21984273HCID 21984273, compound

Product 1

HCID 21984402(7-Bromo-3-nitroquinolin-4-yl)-(5-chloropentyl)amine

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

A suspension of 5-(7-bromo-3-nitroquinolin-4-ylamino)pentan-1-ol (0.92 g, 2.6 mmol) in dichloromethane (13 mL) was cooled to 0° C.; thionyl chloride was added dropwise. The reaction was stirred for five minutes at 0° C. then allowed to warm to ambient temperature and stirred overnight. Saturated aqueous sodium bicarbonate (25 mL) was slowly added followed by water (25 mL). The aqueous layer was separated and extracted with dichloromethane (3×50 mL), and the combined organic fractions were dried over magnesium sulfate and concentrated under reduced pressure to provide 0.91 g of (7-bromo-3-nitroquinolin-4-yl)-(5-chloropentyl)amine as a yellow semisolid.

Workup

  1. temperatureto warm to ambient temperature
  2. stirringstirred overnight
  3. customThe aqueous layer was separated
  4. extractionextracted with dichloromethane (3×50 mL)
  5. dry with materialthe combined organic fractions were dried over magnesium sulfate
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-45a57d7b811b4b1789a26203d86721d9
Source dataset
uspto-grants-2006_08
Patent number
US07091214B2

Reaction notes

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