Acetic Acid → 6-Nitroveratrylidenecyclohexylamine

HRID 1658825Notes

Reaction equation

HRID 1658825 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 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-42f980647856479f9946c78ab836389f
Source dataset
uspto-grants-1976_06
Patent number
US03966760

Reaction notes

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