Acetic Acid → HCID 54476320, compound

HRID 1414745Notes

Reaction equation

HRID 1414745 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-ac38c1bcb0df40e598da0dddd4c719ce
Source dataset
uspto-grants-1977_01
Patent number
US04002652

Reaction notes

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