Pyridine → 8-[2,6-Dichloro-3-(phthalimidoacetylamino)benzyloxy]-2-methylquinoline

HRID 864579Notes

Reaction equation

Cl.Cl.[NH2:3][C:4]1[C:5]([Cl:24])=[C:6]([C:20]([Cl:23])=[CH:21][CH:22]=1)[CH2:7][O:8][C:9]1[CH:10]=[CH:11][CH:12]=[C:13]2[C:18]=1[N:17]=[C:16]([CH3:19])[CH:15]=[CH:14]2.CN1CCCC1=O.N1C=CC=CC=1.[C:38]1(=[O:52])[N:42]([CH2:43][C:44](Cl)=[O:45])[C:41](=[O:47])[C:40]2=[CH:48][CH:49]=[CH:50][CH:51]=[C:39]12>CN(C)C1C=CN=CC=1.O>[Cl:24][C:5]1[C:4]([NH:3][C:44](=[O:45])[CH2:43][N:42]2[C:41](=[O:47])[C:40]3=[CH:48][CH:49]=[CH:50][CH:51]=[C:39]3[C:38]2=[O:52])=[CH:22][CH:21]=[C:20]([Cl:23])[C:6]=1[CH2:7][O:8][C:9]1[CH:10]=[CH:11][CH:12]=[C:13]2[C:18]=1[N:17]=[C:16]([CH3:19])[CH:15]=[CH:14]2

Participants

Conditions

Temperature: 50 °C

Procedure

To a mixture of 8-(3-amino-2,6-dichlorobenzyloxy)-2-methylquinoline dihydrochloride (4.06 g), 4-dimethylaminopyridine (120 mg), N-methylpyrrolidone (30 ml) and pyridine (10 ml) was added phthalimidoacetyl chloride (3.35 g) at ambient temperature. The mixture was stirred at 50° C. for 1.5 hours and cooled in an ice-water bath. Water (40 ml) was added therein and the mixture was stirred for 30 minutes in an ice water bath. The precipitate was collected by vacuum filtration and washed with water and ethyl acetate to give 8-[2,6-dichloro-3-(phthalimidoacetylamino)benzyloxy]-2-methylquinoline (4.45 g) as a yellowish powder.

Workup

temperaturecooled in an ice-water bath
stirringthe mixture was stirred for 30 minutes in an ice water bath
filtrationThe precipitate was collected by vacuum filtration
washwashed with water and ethyl acetate

Sources & evidence

ORD record: ord-6df42987afb54aeeafda9037d5fb286c
Source dataset: uspto-grants-1996_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05563162

Reaction notes

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