Aniline → 2-Methyl-4-phenylimino-3,4-dihydro-2H-quinoline-1-carboxylic Acid Benzyl Ester

HRID 1352486Notes

Reaction equation

HRID 1352486 reaction equation
[CH2:1]([O:8][C:9]([N:11]1[C:20]2[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=2)[C:14](=O)[CH2:13][CH:12]1[CH3:22])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(N(CC)CC)C.[NH2:30][C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1>ClCCl.C1(C)C=CC=CC=1.[Cl-].[Ti+4].[Cl-].[Cl-].[Cl-]>[CH2:1]([O:8][C:9]([N:11]1[C:20]2[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=2)[C:14](=[N:30][C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)[CH2:13][CH:12]1[CH3:22])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

7

Reactant 3

HCID 6115AnilineHCID 8471TriethylamineHCID 120931862-Methyl-4-oxo-3,4-dihydro-2H-quinoline-1-carboxylic Acid Benzyl Ester

Product 1

HCID 120931872-Methyl-4-phenylimino-3,4-dihydro-2H-quinoline-1-carboxylic Acid Benzyl EsterYield 141.7%

Reagents, catalysts & solvents 3

HCID 160960Diamminetetrachlorotitanate(IV)CatalystHCID 1140TolueneSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of 2-Methyl-4-oxo-3,4-dihydro-2H-quinoline-1-carboxylic acid benzyl ester (9 g), triethylamine (24.65 g), aniline (5.7 g) in dichloromethane (110 ml), cooled at −5° C. in an ice/sodium chloride bath, a solution of titanium chloride in toluene 1 mol/l was dropwise added for 10 minutes. The mixture was stirred over night at room temperature and then washed with dichloromethane and an aqueous solution of potassium carbonate. The organic layer was separated, dried over sodium sulfate and the solvent was removed under reduced pressure to give a brown oil (16 g) which was directly used in the next step.

Workup

  1. washwashed with dichloromethane
  2. customThe organic layer was separated
  3. dry with materialdried over sodium sulfate
  4. customthe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-f303626663ca42e89df18b94233eec48
Source dataset
uspto-grants-2007_05
Patent number
US07220760B2

Reaction notes

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