1-Chloro-2-nitrobenzene → N~1~,N~1~-Dimethyl-N~3~-(2-nitrophenyl)propane-1,3-diamine

HRID 1532638Notes

Reaction equation

HRID 1532638 reaction equation
[CH3:1][N:2]([CH3:7])[CH2:3][CH2:4][CH2:5][NH2:6].Cl[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[N+:15]([O-:17])=[O:16]>N1C=CC=CC=1>[CH3:1][N:2]([CH3:7])[CH2:3][CH2:4][CH2:5][NH:6][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[N+:15]([O-:17])=[O:16]

Participants

4

Reactant 2

HCID 69451-Chloro-2-nitrobenzeneHCID 7993N,N-Dimethyl-1,3-propanediamine

Product 1

HCID 210504N~1~,N~1~-Dimethyl-N~3~-(2-nitrophenyl)propane-1,3-diamineYield 99.9%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Conditions

Temperature
125 °C

Procedure

N,N-Dimethyl-1,3-propanediamine (3.24 g) was added to a solution containing 2-chloronitrobenzene (2.00 g) in pyridine (2.56 ml). After being stirred for 13 hours at 120-130° C., the reaction mixture was concentrated. The residue, with toluene added thereto, was washed with saturated sodium hydrogencarbonate aqueous solution and saturated brine successively, dried over sodium sulfate anhydride, and concentrated, thereby yielding the entitled compound (2.83 g) as orange oil.

Workup

  1. concentrationthe reaction mixture was concentrated
  2. additionThe residue, with toluene added
  3. washwas washed with saturated sodium hydrogencarbonate aqueous solution and saturated brine successively
  4. dry with materialdried over sodium sulfate anhydride
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-b6d7659ca5f14c77b27bd24d2b881822
Source dataset
uspto-grants-2001_03
Patent number
US06204264B1

Reaction notes

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