Water → HCID 2755822, compound

HRID 1287651Notes

Reaction equation

HRID 1287651 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([OH:10])=[C:6]([CH:9]=1)[CH:7]=O.C(N)CCC.O.[N+:17]([CH3:20])([O-:19])=[O:18]>C1C=CC=CC=1.C(O)(=O)C>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([OH:10])=[C:6]([CH:9]=1)[CH:7]=[CH:20][N+:17]([O-:19])=[O:18]

Participants

7

Reactant 4

HCID 962WaterHCID 6375NitromethaneHCID 8007ButylamineHCID 124815-Chloro-salicylaldehyde

Product 1

HCID 2755822HCID 2755822, compound

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 241BenzeneSolvent

Procedure

5-Chloro-2-hydroxybenzaldehyde (15.6 g.) and n-butylamine (9.12 g) were refluxed in dry benzene (125 ml.) using Dean-Stark water separator for 3 hours. The benzene phase was concentrated to get the oily intermediate (23 g.). It was refluxed in glacial acetic acid (70 ml.) along with nitromethane (23 ml.) for 1 hour. The crude product was obtained by adding ice-water into the reaction mixture. The crude product was crystallised from benzene. The title product melted at 163-5° C.

Workup

  1. concentrationThe benzene phase was concentrated
  2. customto get the oily intermediate (23 g.)

Sources & evidence

ORD record
ord-015a86b964d54899924a352dd0242d01
Source dataset
uspto-grants-1976_10
Patent number
US03985761

Reaction notes

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