Acetic Acid → 6-Nitroveratrylidenecyclohexylamine

HRID 436448Notes

Reaction equation

HRID 436448 reaction equation
[N+:1]([C:4]1[C:9]([CH:10]=O)=[CH:8][C:7]([O:12][CH3:13])=[C:6]([O:14][CH3:15])[CH:5]=1)([O-:3])=[O:2].[CH:16]1([NH2:22])[CH2:21][CH2:20][CH2:19][CH2:18][CH2:17]1.C(O)(=O)C>C(O)C>[N+:1]([C:4]1[C:9]([CH:10]=[N:22][CH:16]2[CH2:21][CH2:20][CH2:19][CH2:18][CH2:17]2)=[CH:8][C:7]([O:12][CH3:13])=[C:6]([O:14][CH3:15])[CH:5]=1)([O-:3])=[O:2]

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 7965CyclohexylamineHCID 885056-Nitroveratraldehyde

Product 1

HCID 541955546-NitroveratrylidenecyclohexylamineYield 80.4%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A suspension of 42.2 g (0.2 mole) of 6-nitroveratraldehyde, 19.8 g (0.2 mole) cyclohexylamine, 1.0 ml. glacial acetic acid, and 1.25 l. ethanol was stirred and refluxed for 5 min., cooled, and filtered. The solid was washed with 100 ml. cold ethanol and air dried to give 47.0 g (80%) of the product, m.p. 160°-161°.

Workup

  1. temperaturerefluxed for 5 min.
  2. temperaturecooled
  3. filtrationfiltered
  4. washThe solid was washed with 100 ml
  5. dry with materialcold ethanol and air dried

Sources & evidence

ORD record
ord-39de4a89ce6a44ea9392a4f855e2e57d
Source dataset
uspto-grants-1977_02
Patent number
US04009177

Reaction notes

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