Sodium Carbonate → HCID 22320469, compound

HRID 497905Notes

Reaction equation

HRID 497905 reaction equation
Cl[C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[N:5]=[CH:4][C:3]=1[N+:12]([O-:14])=[O:13].Cl.[Cl:16][CH2:17][CH2:18][NH2:19].C(=O)([O-])[O-].[Na+].[Na+]>O>[Cl:16][CH2:17][CH2:18][NH:19][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[N:5]=[CH:4][C:3]=1[N+:12]([O-:14])=[O:13]

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 97937372-Chloroethylamine hydrochlorideHCID 112758084-Chloro-3-nitroquinoline

Product 1

HCID 22320469HCID 22320469, compoundYield 87.8%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Using the general method of Example 1 Part A, 4-chloro-3-nitroquinoline (15.0 g, 71.90 mol) was reacted with 2-chloroethylamine monohydrochloride (8.3 g, 71.90 mmol). The crude product was suspended in water (300 mL) and solid sodium carbonate was added to adjust the pH to 10. The suspension was stirred overnight and then cooled in an ice bath. The solid was then isolated by filtration and washed with chilled water to provide 15.88 g of N-(2-chloroethyl)-3-nitroquinolin-4-amine as a bright yellow fluffy solid.

Workup

  1. temperaturecooled in an ice bath
  2. customThe solid was then isolated by filtration
  3. washwashed with chilled water

Sources & evidence

ORD record
ord-0fdc7534c1e14b379838276e09b0f986
Source dataset
uspto-grants-2005_09
Patent number
US06949649B2

Reaction notes

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