p-Ethoxycarbonylbenzoyl chloride → HCID 10407407, compound

HRID 1586918Notes

Reaction equation

HRID 1586918 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]([CH3:12])[C:7](=[O:13])[CH2:6][C:5]2([CH3:15])[CH3:14].[CH2:16]([O:18][C:19]([C:21]1[CH:29]=[CH:28][C:24]([C:25](Cl)=[O:26])=[CH:23][CH:22]=1)=[O:20])[CH3:17]>N1C=CC=CC=1.O1CCCC1>[CH3:12][N:8]1[C:9]2[C:4](=[CH:3][C:2]([NH:1][C:25]([C:24]3[CH:28]=[CH:29][C:21]([C:19]([O:18][CH2:16][CH3:17])=[O:20])=[CH:22][CH:23]=3)=[O:26])=[CH:11][CH:10]=2)[C:5]([CH3:15])([CH3:14])[CH2:6][C:7]1=[O:13]

Participants

5

Reactant 2

HCID 12276626p-Ethoxycarbonylbenzoyl chlorideHCID 197602276-Amino-1,4,4-trimethyl-3,4-dihydroquinolin-2(1H)-one

Product 1

HCID 10407407HCID 10407407, compoundYield 65.7%

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 8028TetrahydrofuranSolvent

Procedure

37.2 g of 6-amino-3,4-dihydro-1,4,4-trimethyl-2(1H)-quinolinone were dissolved in 600 ml of pyridine and treated dropwise at room temperature with a solution of 43 g of 4-ethoxycarbonylbenzoyl chloride in 80 ml of tetrahydrofuran. After stirring at room temperature for 20 hours, the reaction mixture was poured on to ice-water, extracted several times with ethyl acetate, the organic phase was washed with cold 2N hydrochloric acid and water, dried and evaporated. Chromatography of the crude product (silica gel, eluent hexane/ethyl acetate 2:1, then ethyl acetate) and recrystallization from ethyl acetate/hexane, yielded 45.5 g of ethyl p-[(1,2,3,4-tetrahydro-1,4,4-trimethyl-2-oxo-6-quinolinyl)carbamoyl]-benzoate, m.p. 197°-199° C.

Workup

  1. extractionextracted several times with ethyl acetate
  2. washthe organic phase was washed with cold 2N hydrochloric acid and water
  3. customdried
  4. customevaporated
  5. customChromatography of the crude product (silica gel, eluent hexane/ethyl acetate 2:1, then ethyl acetate) and recrystallization from ethyl acetate/hexane

Sources & evidence

ORD record
ord-9c96a3997ddc4e319205002aeca13d5b
Source dataset
uspto-grants-1993_06
Patent number
US05216148

Reaction notes

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