6-Nitroveratraldehyde → 6-Nitroveratrylidene-2-aminomethyltetrahydropyran

HRID 1658828Notes

Reaction equation

HRID 1658828 reaction equation
[NH2:1][CH2:2][CH:3]1[CH2:8][CH2:7][CH2:6][CH2:5][O:4]1.[N+:9]([C:12]1[C:17]([CH:18]=O)=[CH:16][C:15]([O:20][CH3:21])=[C:14]([O:22][CH3:23])[CH:13]=1)([O-:11])=[O:10]>C(O)C>[N+:9]([C:12]1[C:17]([CH:18]=[C:8]2[CH2:7][CH2:6][CH2:5][O:4][CH:3]2[CH2:2][NH2:1])=[CH:16][C:15]([O:20][CH3:21])=[C:14]([O:22][CH3:23])[CH:13]=1)([O-:11])=[O:10]

Participants

4

Reactant 2

HCID 885056-NitroveratraldehydeHCID 97924(Tetrahydro-2H-pyran-2-ylmethyl)amine

Product 1

HCID 542260806-Nitroveratrylidene-2-aminomethyltetrahydropyran

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

A solution of 2-aminomethyltetrahydropyran (51 g, 0.44 mole) and ethanol (50 ml) was slowly added to a heated suspension of 6-nitroveratraldehyde (84 g, 0.4 mole) and ethanol (600 ml). The resulting solution was refluxed for 1.5 hrs and cooled overnight. The solution was concentrated to dryness and the oil was dissolved in chloroform and washed with water. The chloroform extract was concentrated leaving a dark oil which crystallized upon standing. The solid was suspended in hexane and filtered (117 g, 95%), m.p. 89°-96°.

Workup

  1. temperatureThe resulting solution was refluxed for 1.5 hrs
  2. temperaturecooled overnight
  3. concentrationThe solution was concentrated to dryness
  4. dissolutionthe oil was dissolved in chloroform
  5. washwashed with water
  6. extractionThe chloroform extract
  7. concentrationwas concentrated
  8. customleaving a dark oil which
  9. customcrystallized
  10. filtrationfiltered (117 g, 95%), m.p. 89°-96°

Sources & evidence

ORD record
ord-65d3205aee324baba42a1b00ad564f59
Source dataset
uspto-grants-1976_06
Patent number
US03966760

Reaction notes

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