Benzocaine → Ethyl 3-benzyl-4-hydroxy-2-oxo-1,2-dihydroquinoline-6-carboxylate

HRID 928764

Reaction equation

HRID 928764 reaction equation
[NH2:1][C:2]1[CH:12]=[CH:11][C:5]([C:6]([O:8][CH2:9][CH3:10])=[O:7])=[CH:4][CH:3]=1.[CH2:13]([CH:20]([C:33](OC1C(Cl)=CC(Cl)=CC=1Cl)=[O:34])[C:21](OC1C(Cl)=CC(Cl)=CC=1Cl)=[O:22])[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1>CCOCC>[CH2:13]([C:20]1[C:21](=[O:22])[NH:1][C:2]2[C:3]([C:33]=1[OH:34])=[CH:4][C:5]([C:6]([O:8][CH2:9][CH3:10])=[O:7])=[CH:11][CH:12]=2)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

Participants

4

Reactant 2

HCID 2337BenzocaineHCID 2782299Bis(2,4,6-trichlorophenyl) benzylpropanedioate

Product 1

HCID 54697379Ethyl 3-benzyl-4-hydroxy-2-oxo-1,2-dihydroquinoline-6-carboxylate

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

A mixture of ethyl 4-aminobenzoate (2.85 g, 17.2 mmol) and bis(2,4,6-trichlorophenyl) 2-benzylmalonate (11.4 g, 20.7 mmol, Intermediate 33: step a) was microwaved at 250° C. for 15 minutes (Biotage Initiator). The reaction was then allowed to cool to room temperature, and the resulting tan semisolid was dispersed in ether (15 mL) and filtered. The beige filter cake was washed with ether (1×15 mL) and dried at 100° C. to provide the title compound as a light beige powder.

Workup

  1. customstep a) was microwaved at 250° C. for 15 minutes (Biotage Initiator)
  2. filtrationfiltered
  3. washThe beige filter cake was washed with ether (1×15 mL)
  4. customdried at 100° C.

Sources & evidence

ORD record
ord-2cf16a079a814bd8bd9da47b81f75e4f
Source dataset
uspto-grants-2016_03
Patent number
US09290476B2

Linked notes

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