Aniline → HCID 870654, compound

HRID 1585737Notes

Reaction equation

HRID 1585737 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:8]=[C:9]([O:12][CH3:13])[C:10]=1[OH:11])[CH:6]=O.[NH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1>CO>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:8]=[C:9]([O:12][CH3:13])[C:10]=1[OH:11])[CH:6]=[N:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

Participants

4

Reactant 2

HCID 6115AnilineHCID 8655Syringaldehyde

Product 1

HCID 870654HCID 870654, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

3,5-Dimethoxy-4-hydroxybenzaldehyde (1 g, 5.46 mmol) was dissolved in methanol (50 ml) and aniline (560 mg, 6.01 mmol, 0.35 ml, neat liquid) was added to the solution by syringe. The resultant reaction mixture was stirred overnight at room temperature under nitrogen then taken to dryness in vacuo. The yellow crystals thus obtained were triturated with hot ether, allowed to cool, filtered and the collected solid was washed with ether to yield the title product: 1H NMR (300 MHZ, CDCl3) δ , 8.33 (S, 1H), 7.42-7.39 (m, 2H), 7.21-7.18 (m, 5H), 5.84 (S, 1H), 3.98 (S, 6H).

Workup

  1. customThe resultant reaction mixture
  2. customThe yellow crystals thus obtained
  3. customwere triturated with hot ether
  4. temperatureto cool
  5. filtrationfiltered
  6. washthe collected solid was washed with ether

Sources & evidence

ORD record
ord-4c26316b2399400a9c7171f6329fc981
Source dataset
uspto-grants-1999_08
Patent number
US05939460

Reaction notes

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