Benzocaine → HCID 178468668, compound

HRID 2205170Notes

Reaction equation

HRID 2205170 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([CH:9]([C:14]([C:16]2[CH:21]=[CH:20][C:19]([O:22][CH3:23])=[CH:18][CH:17]=2)=O)[C:10](OC)=[O:11])=[CH:5][CH:4]=1.[NH2:24][C:25]1[CH:35]=[CH:34][C:28]([C:29]([O:31][CH2:32][CH3:33])=[O:30])=[CH:27][CH:26]=1.CS(O)(=O)=O>O(C1C=CC=CC=1)C1C=CC=CC=1>[OH:11][C:10]1[C:35]2[C:25](=[CH:26][CH:27]=[C:28]([C:29]([O:31][CH2:32][CH3:33])=[O:30])[CH:34]=2)[N:24]=[C:14]([C:16]2[CH:17]=[CH:18][C:19]([O:22][CH3:23])=[CH:20][CH:21]=2)[C:9]=1[C:6]1[CH:7]=[CH:8][C:3]([O:2][CH3:1])=[CH:4][CH:5]=1

Participants

5

Reactant 3

HCID 2337BenzocaineHCID 6395Methanesulfonic AcidHCID 86718153HCID 86718153, compound

Product 1

HCID 178468668HCID 178468668, compoundYield 62.2%

Reagents, catalysts & solvents 1

HCID 7583Diphenyl EtherSolvent

Conditions

Temperature
90 °C

Procedure

Methyl 2,3-bis(4-methoxyphenyl)-3-oxopropanoate (1.3 g, 4.14 mmol, 1.00 equiv), ethyl 4-aminobenzoate (680 mg, 4.12 mmol, 1.00 equiv), CH3SO3H (118 mg, 1.23 mmol, 0.30 equiv), and Ph2O (20 mL) were placed in a 100-mL round-bottom flask stirred for 1 h at 90° C., then at 180° C. for 3 h, in an oil bath. Upon cooling, 100 ml of petroleum ether was added. The resulting solid was collected by filtration and dried in a vacuum oven, affording 1.1 g (crude) of ethyl 4-hydroxy-2,3-bis(4-methoxyphenyl)quinoline-6-carboxylate as a brown solid.

Workup

  1. waitat 180° C. for 3 h
  2. temperatureUpon cooling
  3. filtrationThe resulting solid was collected by filtration
  4. customdried in a vacuum oven

Sources & evidence

ORD record
ord-5b5e6e573ced438d9df1f5bd98157081
Source dataset
uspto-grants-2016_06
Patent number
US09370522B2

Reaction notes

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