Water → HCID 46830485, compound

HRID 388579Notes

Reaction equation

HRID 388579 reaction equation
[Cl:1][C:2]1[C:11]([N+:12]([O-:14])=[O:13])=[C:10](Cl)[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[N:3]=1.C(N(CC)CC)C.[CH2:23]([NH2:30])[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1.O>CN(C)C=O>[CH2:23]([NH:30][C:10]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[N:3]=[C:2]([Cl:1])[C:11]=1[N+:12]([O-:14])=[O:13])[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1

Participants

6

Reactant 4

HCID 962WaterHCID 7504BenzylamineHCID 8471TriethylamineHCID 27851382,4-Dichloro-3-nitroquinoline

Product 1

HCID 46830485HCID 46830485, compoundYield 101.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 2,4-dichloro-3-nitroquinoline (25 g, 0.10 mol) in N,N-dimethylformamide (DMF) (130 mL) was cooled to 0° C. Triethylamine (17.2 mL, 0.123 mol) and benzylamine (11.2 mL, 0.10 mol) were sequentially added, and the reaction was stirred at ambient temperature overnight. The reaction was poured into water (1 L), and the suspension was stirred for 30 minutes at room temperature. The resulting precipitate was isolated by filtration and washed with water to provide 31.92 g of N-benzyl-2-chloro-3-nitroquinolin-4-amine as a bright yellow powder.

Workup

  1. stirringthe suspension was stirred for 30 minutes at room temperature
  2. customThe resulting precipitate was isolated by filtration
  3. washwashed with water

Sources & evidence

ORD record
ord-632ccc08e33f4450af9ba710c6d50b7c
Source dataset
uspto-grants-2013_02
Patent number
US08377957B2

Reaction notes

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