Benzaldehyde → HCID 19787430, compound

HRID 1657234Notes

Reaction equation

HRID 1657234 reaction equation
[NH2:1][C:2]1[C:3]([F:10])=[CH:4][C:5]([Cl:9])=[C:6]([OH:8])[CH:7]=1.[CH:11](=O)[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1>C1(C)C=CC(S(O)(=O)=O)=CC=1.C1(C)C=CC=CC=1>[CH:11](=[N:1][C:2]1[C:3]([F:10])=[CH:4][C:5]([Cl:9])=[C:6]([OH:8])[CH:7]=1)[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

Participants

5

Reactant 2

HCID 240BenzaldehydeHCID 1586545-Amino-2-chloro-4-fluorophenol

Product 1

HCID 19787430HCID 19787430, compoundYield 94.5%

Reagents, catalysts & solvents 2

HCID 6101p-Toluenesulfonic acidCatalystHCID 1140TolueneSolvent

Procedure

A 50-ml four-neck flask equipped with a dehydrating column was charged with 5-amino-2-chloro-4-fluorophenol (1 g), benzaldehyde (0.68 g), p-toluenesulfonic acid (10 mg) and toluene (50 g). The mixture was dehydrated under reflux under normal pressure for 5 hours, and then concentrated under reduced pressure. The precipitated crystals were filtered and washed with a small amount of hexane to give 1.46 g of 5-benzylidenamino-2-chloro-4-fluorophenol as pale brown needle crystals (yield, 94.5%), m.p., 157°-159° C.; MS (m/z) 249 (M+) 172; NMR (CDCl3, δ): 5.1-5.8 (broad, 1H), 6.83 (d, 1H, J=7.6 Hz), 7.15 (d, 1H, J=9.6 Hz), 7.4-7.6 (m, 3H), 7.8-8.0 (m, 2H), 8.47 (s, 1H).

Workup

  1. customA 50-ml four-neck flask equipped with a dehydrating column
  2. temperatureunder reflux under normal pressure for 5 hours
  3. concentrationconcentrated under reduced pressure
  4. filtrationThe precipitated crystals were filtered
  5. washwashed with a small amount of hexane
  6. customto give

Sources & evidence

ORD record
ord-dae41cdfb16b40e584c713f5fcb272c4
Source dataset
uspto-grants-1993_10
Patent number
US05256822

Reaction notes

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