2-Methoxyethylamine → HCID 20494217, compound

HRID 1075137Notes

Reaction equation

HRID 1075137 reaction equation
C([O:3][C:4](=[O:17])[C:5]1[CH:13]=[C:12]([N+:14]([O-:16])=[O:15])[CH:11]=[C:7]([C:8]([NH2:10])=[O:9])[CH:6]=1)C.[CH3:18][O:19][CH2:20][CH2:21]N>>[N+:14]([C:12]1[CH:11]=[C:7]([C:8]([NH:10][CH2:21][CH2:20][O:19][CH3:18])=[O:9])[CH:6]=[C:5]([CH:13]=1)[C:4]([OH:3])=[O:17])([O-:16])=[O:15]

Participants

3

Reactant 2

HCID 80182-MethoxyethylamineHCID 20494213HCID 20494213, compound

Product 1

HCID 20494217HCID 20494217, compoundYield 81.1%

Procedure

239.2 g (1 mole) of 5-nitroisophthalamic-acid-monoethylester is dissolved in 444 ml (5 moles) of 2-methoxyethylamine, the temperature rising to 60° C. After stirring for 2 days at room temperature, the mixture is evaporated in vacuum at 70° C., dissolved with 2.4 liters of water, adjusted to a pH of 7 by means of hydrochloric acid, treated with charcoal and then acidified to a pH of 1 with 12 N hydrochloric acid. The precipitate provides 217.6 g (81.1% of theoretical) of 5-nitro-N-(2-methoxyethyl)-isophthalamic acid; m.p.=203°-207° C.

Workup

  1. customrising to 60° C
  2. customthe mixture is evaporated in vacuum at 70° C.
  3. dissolutiondissolved with 2.4 liters of water
  4. additiontreated with charcoal

Sources & evidence

ORD record
ord-327845f9b120464ba42e81543405f8ad
Source dataset
uspto-grants-1983_07
Patent number
US04395391

Reaction notes

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