Triethylamine → 1-Acetyl-4-[(benzoxazol-5-yl)imino]-2-methyl-1,2,3,4-tetrahydroquinoline

HRID 1629674

Reaction equation

HRID 1629674 reaction equation
[C:1]([N:4]1[C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[C:7](=O)[CH2:6][CH:5]1[CH3:15])(=[O:3])[CH3:2].[NH2:16][C:17]1[CH:18]=[CH:19][C:20]2[O:24][CH:23]=[N:22][C:21]=2[CH:25]=1.C(N(CC)CC)C>C(Cl)Cl.[Ti](Cl)(Cl)(Cl)Cl>[C:1]([N:4]1[C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[C:7](=[N:16][C:17]2[CH:18]=[CH:19][C:20]3[O:24][CH:23]=[N:22][C:21]=3[CH:25]=2)[CH2:6][CH:5]1[CH3:15])(=[O:3])[CH3:2]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 5895634(1H)-Quinolinone, 1-acetyl-2,3-dihydro-2-methyl-HCID 14821881,3-Benzoxazol-5-amine

Product 1

HCID 666251671-Acetyl-4-[(benzoxazol-5-yl)imino]-2-methyl-1,2,3,4-tetrahydroquinoline

Reagents, catalysts & solvents 2

HCID 24193Titanium TetrachlorideCatalystHCID 6344DichloromethaneSolvent

Procedure

[Step 1] 177 mg of 1-acetyl-4-oxo-2-methyl-1,2,3,4-tetrahydroquinoline and 77 mg of 5-aminobenzoxazole were dissolved in 2 mL of methylene chloride, and 0.32 mL of triethylamine and 0.57 mL of titanium tetrachloride (1.0 M dichloromethane solution) were added to the solution under ice cooling. The mixture was stirred for 16 hours at room temperature. After completion of the reaction, the reaction liquid was filtered through Celite, and was concentrated under reduced pressure. Thus, a crude product of 1-acetyl-4-[(benzoxazol-5-yl)imino]-2-methyl-1,2,3,4-tetrahydroquinoline was obtained as a pale brown solid.

Workup

  1. customAfter completion of the reaction
  2. customthe reaction liquid
  3. filtrationwas filtered through Celite
  4. concentrationwas concentrated under reduced pressure

Sources & evidence

ORD record
ord-fd753f7fcee6499ea2392a280f58a010
Source dataset
uspto-grants-2014_07
Patent number
US08791090B2

Linked notes

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