Hydrochloric Acid → Ethyl 4-(3-chlorophenyl)-1,2-dihydro-2-oxo-6-[(4-phenyl-2-thiazolyl)carbonyl]-3-quinolinecarboxylate

HRID 1830806Notes

Reaction equation

HRID 1830806 reaction equation
[CH2:1]([O:3][C:4](=[O:37])[CH2:5][C:6](=[O:36])[NH:7][C:8]1[CH:13]=[CH:12][C:11]([C:14]([C:16]2[S:17][CH:18]=[C:19]([C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)[N:20]=2)=[O:15])=[CH:10][C:9]=1[C:27](=O)[C:28]1[CH:33]=[CH:32][CH:31]=[C:30]([Cl:34])[CH:29]=1)[CH3:2].CC(O)(C)C.[K].Cl>COCCOC>[Cl:34][C:30]1[CH:29]=[C:28]([C:27]2[C:9]3[C:8](=[CH:13][CH:12]=[C:11]([C:14]([C:16]4[S:17][CH:18]=[C:19]([C:21]5[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=5)[N:20]=4)=[O:15])[CH:10]=3)[NH:7][C:6](=[O:36])[C:5]=2[C:4]([O:3][CH2:1][CH3:2])=[O:37])[CH:33]=[CH:32][CH:31]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 6386tert-ButanolHCID 5462222PotassiumHCID 22048474N-[2-(3-chlorobenzoyl)-4-[(4-phenyl-2-thiazolyl)carbonyl]phenyl]-3-oxo-beta-alanine ethyl ester

Product 1

HCID 22048464Ethyl 4-(3-chlorophenyl)-1,2-dihydro-2-oxo-6-[(4-phenyl-2-thiazolyl)carbonyl]-3-quinolinecarboxylateYield 70%

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent

Procedure

A mixture of intermediate (17) (0.048 mol) in DME (250 ml) was cooled on an ice bath and 2-methyl-2-propanol, potassium salt (0.096 mol) was added portionwise. The mixture was stirred at a low temperature for 15 min, poured out into ice water and acidified with HCl 3N. The precipitate was filtered off, washed with water, pasted up with CH3CN and diethyl ether, then dried, yielding 17.3 g (70%) of ethyl 4-(3-chlorophenyl)-1,2-dihydro-2-oxo-6-[(4-phenyl-2-thiazolyl)carbonyl]-3-quinolinecarboxylate (intermediate 18), mp 261° C.

Workup

  1. temperaturewas cooled on an ice bath
  2. filtrationThe precipitate was filtered off
  3. washwashed with water
  4. customdried

Sources & evidence

ORD record
ord-2d1c8edcb2c944b5a75a2d2e8d204d48
Source dataset
uspto-grants-2006_06
Patent number
US07067531B2

Reaction notes

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