N,N-Dimethyl-1,3-propanediamine → HCID 22013769, compound

HRID 1532657Notes

Reaction equation

HRID 1532657 reaction equation
[CH3:1][N:2]([CH3:7])[CH2:3][CH2:4][CH2:5][NH2:6].Cl[C:9]1[CH:19]=[CH:18][C:12]([C:13]([O:15][CH2:16][CH3:17])=[O:14])=[CH:11][C:10]=1[N+:20]([O-:22])=[O:21]>C(OCC)(=O)C>[CH3:1][N:2]([CH3:7])[CH2:3][CH2:4][CH2:5][NH:6][C:9]1[CH:19]=[CH:18][C:12]([C:13]([O:15][CH2:16][CH3:17])=[O:14])=[CH:11][C:10]=1[N+:20]([O-:22])=[O:21]

Participants

4

Reactant 2

HCID 7993N,N-Dimethyl-1,3-propanediamineHCID 1268247Ethyl 4-chloro-3-nitrobenzoate

Product 1

HCID 22013769HCID 22013769, compoundYield 101.2%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
125 °C

Procedure

N,N-Dimethy-1,3-propanediamine (1.41 g) was added to ethyl 4-chloro-3-nitrobenzoate (1.59 g) and stirred for 12 hours at 125° C. The reaction mixture, with ethyl acetate added thereto, was washed with 1N sodium hydroxide aqueous solution, water, and saturated brine successively, dried over sodium sulfate anhydride, and concentrated, thereby yielding the entitled compound (2.07 g) as brown oil.

Workup

  1. washwas washed with 1N sodium hydroxide aqueous solution, water, and saturated brine successively
  2. dry with materialdried over sodium sulfate anhydride
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-1f6d9195e4494539b03d21d4b032ff02
Source dataset
uspto-grants-2001_03
Patent number
US06204264B1

Reaction notes

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