Hydrochloric Acid → 4-nitro-2-methoxy-N-(beta-aminoethyl)aniline

HRID 436336Notes

Reaction equation

HRID 436336 reaction equation
Cl[C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][C:3]=1[O:11][CH3:12].O.[CH2:14]([NH2:17])[CH2:15][NH2:16].C(N)CN.Cl>>[N+:8]([C:5]1[CH:6]=[CH:7][C:2]([NH:16][CH2:15][CH2:14][NH2:17])=[C:3]([O:11][CH3:12])[CH:4]=1)([O-:10])=[O:9]

Participants

5

Reactant 4

HCID 313Hydrochloric AcidHCID 3301EthylenediamineHCID 705192-Chloro-5-nitroanisoleHCID 12200817Ethylenediamine monohydrate

Product 1

HCID 214541994-nitro-2-methoxy-N-(beta-aminoethyl)anilineYield 86.1%

Procedure

31 g (0.165 mole) of 2-chloro-5-nitro-anisole is added to 130 cm3 (1.65 mole) ethylenediamine hydrate. The reaction mixture is heated at reflux for five hours, and the excess of ethylenediamine driven off under vacuum. The residue is treated with 200 cm3 of a 5N hydrochloric acid solution, and dried, yielding 30 g of 4-nitro-2-methoxy-N(β-aminoethyl) aniline, which is washed with acetone.

Workup

  1. temperatureThe reaction mixture is heated
  2. temperatureat reflux for five hours
  3. customdried

Sources & evidence

ORD record
ord-9f073526c25e487a8ba76f1aeac338f3
Source dataset
uspto-grants-1977_02
Patent number
US04008272

Reaction notes

Loading…