Water → HCID 46830485, compound

HRID 415449Notes

Reaction equation

HRID 415449 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-fad6b49bd8b5467ea8acb249f96c0e5f
Source dataset
uspto-grants-2012_01
Patent number
US08088790B2

Reaction notes

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