4-Chloro-3-nitrotoluene → HCID 43349363, compound

HRID 1532671Notes

Reaction equation

HRID 1532671 reaction equation
[CH3:1][N:2]([CH3:7])[CH2:3][CH2:4][CH2:5][NH2:6].Cl[C:9]1[CH:14]=[CH:13][C:12]([CH3:15])=[CH:11][C:10]=1[N+:16]([O-:18])=[O:17]>C1(C)C=CC=CC=1>[CH3:1][N:2]([CH3:7])[CH2:3][CH2:4][CH2:5][NH:6][C:9]1[CH:14]=[CH:13][C:12]([CH3:15])=[CH:11][C:10]=1[N+:16]([O-:18])=[O:17]

Participants

4

Reactant 2

HCID 69764-Chloro-3-nitrotolueneHCID 7993N,N-Dimethyl-1,3-propanediamine

Product 1

HCID 43349363HCID 43349363, compoundYield 92.4%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
125 °C

Procedure

N,N-Dimethyl-1,3-propanediamine (5.114 g) was added to 4-chloro-3-nitrotoluene (3.434 g) and the mixture was stirred for 14 hours at 125° C. The reaction mixture, with toluene added thereto, was washed with saturated sodium hydrogencarbonate aqueous solution and saturated brine successively, dried over sodium sulfate anhydride, and concentrated. The residue (4.93 g) was purified by silica gel column chromatography (silica gel 50 g, chloroform:methanol=1:0-10:1), thereby yielding the entitled compound (4.39 g) as reddish orange oil.

Workup

  1. washwas washed with saturated sodium hydrogencarbonate aqueous solution and saturated brine successively
  2. dry with materialdried over sodium sulfate anhydride
  3. concentrationconcentrated
  4. customThe residue (4.93 g) was purified by silica gel column chromatography (silica gel 50 g, chloroform:methanol=1:0-10:1)

Sources & evidence

ORD record
ord-1aca5b1758e64074bf2fb66e6243b3d2
Source dataset
uspto-grants-2001_03
Patent number
US06204264B1

Reaction notes

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