Acetic Acid → 6-Nitroveratrylidenecyclohexylamine

HRID 597494Notes

Reaction equation

HRID 597494 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 1. ethanol was stirred and refluxed for five 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 five 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-b2258f2183274283b762899ab9e0f7af
Source dataset
uspto-grants-1977_03
Patent number
US04014878

Reaction notes

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