Aniline → HCID 870654, compound

HRID 1603741Notes

Reaction equation

HRID 1603741 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-1e030346cf734b45817c3ab564335f57
Source dataset
uspto-grants-1999_11
Patent number
US05990137

Reaction notes

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