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

HRID 2049529

Reaction equation

HRID 2049529 reaction equation
[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]

Participants

4

Reactant 2

HCID 68943-Chloro-2-methylanilineHCID 6998Salicylaldehyde

Product 1

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

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-d76861eb1dea437e8bad2d4ff0581f28
Source dataset
uspto-grants-1980_04
Patent number
US04198349

Linked notes

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