Acetic Acid → HCID 54476320, compound

HRID 597497Notes

Reaction equation

HRID 597497 reaction equation
[NH2:1][CH2:2][CH2:3][CH2:4][N:5]1[CH2:10][CH2:9][O:8][CH2:7][CH2:6]1.C(O)C.[N+:14]([C:17]1[C:22]([CH:23]=O)=[CH:21][C:20]([O:25][CH3:26])=[C:19]([O:27][CH3:28])[CH:18]=1)([O-:16])=[O:15].C(O)(=O)C>C(Cl)(Cl)Cl>[N+:14]([C:17]1[C:22]([CH:23]=[C:6]2[CH2:7][O:8][CH2:9][CH2:10][N:5]2[CH2:4][CH2:3][CH2:2][NH2:1])=[CH:21][C:20]([O:25][CH3:26])=[C:19]([O:27][CH3:28])[CH:18]=1)([O-:16])=[O:15]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 702Ethanol2×HCID 61055N-(3-Aminopropyl)morpholineHCID 885056-Nitroveratraldehyde

Product 1

HCID 54476320HCID 54476320, compoundYield 95%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

A solution of N-(γ-aminopropyl)morpholine (63 g, 0.44 mole) and ethanol (50 ml) was introduced to a heated suspension of 6-nitroveratraldehyde (84 g, 0.4 mole), ethanol (600 ml) and acetic acid (1 ml). The resulting solution was refluxed for 1.5 hrs and allowed to cool overnight. The solvent was stripped leaving a dark oil which was dissolved in chloroform (300 ml) and washed with water. The chloroform was stripped giving 127 g (95%) of the product.

Workup

  1. temperatureThe resulting solution was refluxed for 1.5 hrs
  2. temperatureto cool overnight
  3. customThe solvent was stripped leaving a dark oil which
  4. washwashed with water

Sources & evidence

ORD record
ord-141a3c81972645eb9ffe178ef4f8841f
Source dataset
uspto-grants-1977_03
Patent number
US04014878

Reaction notes

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