Phenylacetaldehyde → HCID 23440873, compound

HRID 1358011Notes

Reaction equation

HRID 1358011 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][CH2:9][CH2:10][C:11]2[CH:12]=[C:13]([OH:17])[CH:14]=[CH:15][CH:16]=2)=[CH:4][CH:3]=1.[C:18]1([CH2:24][CH:25]=O)[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1.FC(F)(F)C(O)=O>C(Cl)Cl>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[CH2:9][CH2:10][C:11]3[C:16](=[CH:15][CH:14]=[C:13]([OH:17])[CH:12]=3)[CH:25]2[CH2:24][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 998PhenylacetaldehydeHCID 6422Trifluoroacetic acidHCID 234407953-[2-(4-Chloroanilino)ethyl]phenol

Product 1

HCID 23440873HCID 23440873, compoundYield 72.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 3-{2-[(4-chlorophenyl)amino]ethyl}phenol (0.20 g, 0.8 mmol) and phenylacetaldehyde (0.194 g, 1.6 mmol) in CH2Cl2 (6 mL) was added trifluoroacetic acid (0.148 g, 1.6 mmol). After stirring at room temperature overnight, the reaction was quenched with saturated sodium bicarbonate and extracted with CH2Cl2. The organic layer was dried over MgSO4, filtered, and concentrated. The residue was purified by chromatography (SiO2, 15-30% ethyl acetate/hexane) to provide the title compound (0.203 g, 72% yield): 1H NMR (CDCl3) 7.19-7.24 (m, 4H), 7.16 (m, 1H), 7.14 (m, 1H), 6.70 (m, 2H), 6.71 (m, 2H), 6.61 (m, 2H), 6.54 (dd, 1H), 4.77 (t, 1H), 3.58 (ddd, 1H), 3.47 (ddd, 1H), 3.17 (dd, 1H), 2.86-2.99 (m, 2H), 2.67 (m, 1H); ES-MS (m/z) 350 [M+H]+.

Workup

  1. customthe reaction was quenched with saturated sodium bicarbonate
  2. extractionextracted with CH2Cl2
  3. dry with materialThe organic layer was dried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe residue was purified by chromatography (SiO2, 15-30% ethyl acetate/hexane)

Sources & evidence

ORD record
ord-74de4092d41c4d689733493ca16c0e09
Source dataset
uspto-grants-2003_07
Patent number
US06593322B1

Reaction notes

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