3-Chloro-2-methylaniline → N-(p-carbomethoxybenzylidene)-2-methyl-3-chloroaniline

HRID 2050199Notes

Reaction equation

HRID 2050199 reaction equation
[C:1]([C:5]1[CH:12]=[CH:11][C:8]([CH:9]=O)=[CH:7][CH:6]=1)([O:3][CH3:4])=[O:2].[CH3:13][C:14]1[C:20]([Cl:21])=[CH:19][CH:18]=[CH:17][C:15]=1[NH2:16]>C(O)C>[C:1]([C:5]1[CH:12]=[CH:11][C:8]([CH:9]=[N:16][C:15]2[CH:17]=[CH:18][CH:19]=[C:20]([Cl:21])[C:14]=2[CH3:13])=[CH:7][CH:6]=1)([O:3][CH3:4])=[O:2]

Participants

4

Reactant 2

HCID 68943-Chloro-2-methylanilineHCID 15294Methyl 4-Formylbenzoate

Product 1

HCID 20342435N-(p-carbomethoxybenzylidene)-2-methyl-3-chloroaniline

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

p-carbomethoxybenzaldehye (0.20 moles) was treated with 2-methyl-3-chloroaniline (0.20 moles) 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 hours. The crystals which formed were collected, washed with 95% ethanol, and air dried. Recrystallization from 95% ethanol gave N-(p-carbomethoxybenzylidene)-2-methyl-3-chloroaniline.

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 hours
  5. customThe crystals which formed
  6. customwere collected
  7. washwashed with 95% ethanol, and air
  8. customdried
  9. customRecrystallization from 95% ethanol

Sources & evidence

ORD record
ord-e93b622876df4c318633c20b07faf69d
Source dataset
uspto-grants-1980_04
Patent number
US04200648

Reaction notes

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