1-Naphthylamine → HCID 22022775, compound

HRID 1793628Notes

Reaction equation

HRID 1793628 reaction equation
[C:1]([C:9]1[C:10](C(=O)C2C=CC=CC=2)=[N:11][CH:12]=[CH:13][CH:14]=1)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:23]1([NH2:33])[C:32]2[C:27](=[CH:28][CH:29]=[CH:30][CH:31]=2)[CH:26]=[CH:25][CH:24]=1>C1(C)C=CC=CC=1.Cl[Ti](Cl)(Cl)Cl>[C:1]([C:9]1[CH:10]=[N:11][C:12](=[N:33][C:23]2[C:32]3[C:27](=[CH:28][CH:29]=[CH:30][CH:31]=3)[CH:26]=[CH:25][CH:24]=2)[C:13](=[N:33][C:23]2[C:32]3[C:27](=[CH:28][CH:29]=[CH:30][CH:31]=3)[CH:26]=[CH:25][CH:24]=2)[C:14]=1[C:1](=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 86401-NaphthylamineHCID 22022776HCID 22022776, compound

Product 1

HCID 22022775HCID 22022775, compound

Reagents, catalysts & solvents 2

HCID 24193Titanium TetrachlorideCatalystHCID 1140TolueneSolvent2×

Procedure

TiCl4 (0.4 ml, 3.5 mmol) in toluene (20 ml) was added to a mixture of dibenzoylpyridine (0.91 g, 3.2 mmol) and 1-naphthylamine (2.90 g, 17 mmol) in toluene (50 ml) at 0° C. After the addition was complete, the reaction was stirred at room temperature for 1 hour and then under refluxed for 3 hours. The solid was filtered and washed with toluene. The solvent was removed under vacuum. The ligand was isolated after the column chromatography (hexane/ethyl acetate=5/1) to produce a yield of 0.65 g.

Workup

  1. additionAfter the addition
  2. temperatureunder refluxed for 3 hours
  3. filtrationThe solid was filtered
  4. washwashed with toluene
  5. customThe solvent was removed under vacuum
  6. customThe ligand was isolated after the column chromatography (hexane/ethyl acetate=5/1)
  7. customto produce a yield of 0.65 g

Sources & evidence

ORD record
ord-aa57b35910cb4d42b28c1f5616ac8b8a
Source dataset
uspto-grants-2006_07
Patent number
US07081506B2

Reaction notes

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