Benzaldehyde → HCID 178489586, compound

HRID 41326Notes

Reaction equation

HRID 41326 reaction equation
[CH:1](=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:9][O:10][C:11]1[CH:17]=[CH:16][CH:15]=[CH:14][C:12]=1[NH2:13]>C1(C)C=CC=CC=1>[CH3:9][O:10][C:11]1[CH:17]=[CH:16][CH:15]=[CH:14][C:12]=1/[N:13]=[CH:1]/[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 240BenzaldehydeHCID 70002-Methoxyaniline

Product 1

HCID 178489586HCID 178489586, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A mixture of 31.8 g (0.30 mol) of benzaldehyde, 36.9 g (0.30 g) of 2-methoxyaniline and 450 mL of toluene was refluxed using a Dean-Stark head for 1 hr. 15 granules of 4A molecular sieves were added. This mixture was refluxed for 4 hr, then filtered off, and the filtrate was evaporated to dryness. The residue was dried in vacuum at 70° C. This crude product was further used without an additional purification, since it is unstable on silica gel 60 and decomposes when dried under vacuum. Yield 52.0 g (82%) of the title material.

Workup

  1. temperaturewas refluxed
  2. customfor 1 hr
  3. temperatureThis mixture was refluxed for 4 hr
  4. filtrationfiltered off
  5. customthe filtrate was evaporated to dryness
  6. customThe residue was dried in vacuum at 70° C
  7. customThis crude product was further used without an additional purification, since it
  8. customdried under vacuum

Sources & evidence

ORD record
ord-c8f4ee2ab0a142a4b1a7590925e67ed8
Source dataset
uspto-grants-2013_09
Patent number
US08530593B2

Reaction notes

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