1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → 8-[2,6-dichloro-3-[N-(2-phthalimidoethyl)carbamoyl]benzyloxy]-2-methylquinoline

HRID 613655Notes

Reaction equation

HRID 613655 reaction equation
[Cl:1][C:2]1[C:20]([C:21]([OH:23])=O)=[CH:19][CH:18]=[C:17]([Cl:24])[C:3]=1[CH2:4][O:5][C:6]1[CH:7]=[CH:8][CH:9]=[C:10]2[C:15]=1[N:14]=[C:13]([CH3:16])[CH:12]=[CH:11]2.C(N=C=NCCCN(C)C)C.ON1C2C=CC=CC=2N=N1.Cl.[NH2:47][CH2:48][CH2:49][N:50]1[C:54](=[O:55])[C:53]2=[CH:56][CH:57]=[CH:58][CH:59]=[C:52]2[C:51]1=[O:60].C(=O)(O)[O-].[Na+]>CN(C)C=O>[Cl:1][C:2]1[C:20]([C:21](=[O:23])[NH:47][CH2:48][CH2:49][N:50]2[C:54](=[O:55])[C:53]3=[CH:56][CH:57]=[CH:58][CH:59]=[C:52]3[C:51]2=[O:60])=[CH:19][CH:18]=[C:17]([Cl:24])[C:3]=1[CH2:4][O:5][C:6]1[CH:7]=[CH:8][CH:9]=[C:10]2[C:15]=1[N:14]=[C:13]([CH3:16])[CH:12]=[CH:11]2

Participants

7

Reactant 5

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 516892Sodium BicarbonateHCID 183218388-(2,6-Dichloro-3-carboxybenzyloxy)-2-methylquinolineHCID 220638492-(2-Aminoethyl)-1H-isoindole-1,3(2H)-dione--hydrogen chloride (1/1)

Product 1

HCID 183218478-[2,6-dichloro-3-[N-(2-phthalimidoethyl)carbamoyl]benzyloxy]-2-methylquinolineYield 88.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a suspension of 8-(2,6-dichloro-3-carboxybenzyloxy)-2-methylquinoline (800 mg), 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide (508 mg) and 1-hydroxybenzotriazole (388 mg) in N,N-dimethylformamide (8 ml) was added N-(2-aminoethyl)phthalimide hydrochloride (551 mg), and the mixture was stirred for 3 hours at ambient temperature. To the reaction mixture was added saturated sodium bicarbonate solution, and the mixture was extracted with chloroform. The insoluble material was filtered off, and the filtrate was washed with water, dried over magnesium sulfate and evaporated in vacuo. The residue was crystallized from ethyl acetate to give 8-[2,6-dichloro-3-[N-(2-phthalimidoethyl)carbamoyl]benzyloxy]-2-methylquinoline (1.04 g) as colorless crystals.

Workup

  1. extractionthe mixture was extracted with chloroform
  2. filtrationThe insoluble material was filtered off
  3. washthe filtrate was washed with water
  4. dry with materialdried over magnesium sulfate
  5. customevaporated in vacuo
  6. customThe residue was crystallized from ethyl acetate

Sources & evidence

ORD record
ord-f4305ac1ec6c4a48bc733e2ca809dbba
Source dataset
uspto-grants-1999_12
Patent number
US06008229

Reaction notes

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