3-Chloro-2-methylaniline → 2-{[(3-Chloro-2-methylphenyl)imino]methyl}phenol

HRID 225179

Reaktionsgleichung

Reaktionsgleichung von HRID 225179
[OH:1][C:2]1[CH:9]=[CH:8][CH:7]=[CH:6][C:3]=1[CH:4]=O.[CH3:10][C:11]1[C:17]([Cl:18])=[CH:16][CH:15]=[CH:14][C:12]=1[NH2:13]>C(O)C>[OH:1][C:2]1[CH:9]=[CH:8][CH:7]=[CH:6][C:3]=1[CH:4]=[N:13][C:12]1[CH:14]=[CH:15][CH:16]=[C:17]([Cl:18])[C:11]=1[CH3:10]

Komponenten

4

Edukt 2

HCID 68943-Chloro-2-methylanilineHCID 6998Salicylaldehyde

Produkt 1

HCID 2963922-{[(3-Chloro-2-methylphenyl)imino]methyl}phenol

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

o-Hydroxybenzaldehyde (0.20 mole) was treated with 2-methyl-3-chloroaniline (0.20 mole) with vigorous stirring in a 1 liter Erlenmeyer flask. After 15 mins., 33 cc of 95% ethanol was added and the reaction mixture was stirred vigorously for an additional 45 mins. The reaction mixture was left standing at room temperature for 10 min., then it was placed in an ice-bath for 0.5 hour. The crystals which formed were collected, washed with 95% ethanol, and air dried. Recrystallization from 85% ethanol gave N-(o-hydroxybenzylidene)-2-methyl-3-chloroaniline. m.p. 95°-97° C.

Aufarbeitung

  1. stirringthe reaction mixture was stirred vigorously for an additional 45 mins
  2. waitThe reaction mixture was left
  3. waitstanding at room temperature for 10 min.
  4. waitit was placed in an ice-bath for 0.5 hour
  5. customThe crystals which formed
  6. customwere collected
  7. washwashed with 95% ethanol, and air
  8. customdried
  9. customRecrystallization from 85% ethanol

Quellen und Nachweise

ORD-Eintrag
ord-c4cad60feea44fb8b0ecc89b55284f0c
Quelldatensatz
uspto-grants-1980_11
Patentnummer
US04235929

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