Benzocaine → Ethyl 4-(quinoline-8-sulfonamido)benzoate

HRID 1626326

Reaction equation

HRID 1626326 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.[N:13]1[C:22]2[C:17](=[CH:18][CH:19]=[CH:20][C:21]=2[S:23](Cl)(=[O:25])=[O:24])[CH:16]=[CH:15][CH:14]=1>N1C=CC=CC=1>[N:13]1[C:22]2[C:17](=[CH:18][CH:19]=[CH:20][C:21]=2[S:23]([NH:1][C:2]2[CH:3]=[CH:4][C:5]([C:6]([O:8][CH2:9][CH3:10])=[O:7])=[CH:11][CH:12]=2)(=[O:25])=[O:24])[CH:16]=[CH:15][CH:14]=1

Participants

4

Reactant 2

HCID 2337BenzocaineHCID 292208-Quinolinesulfonyl chloride

Product 1

HCID 1357549Ethyl 4-(quinoline-8-sulfonamido)benzoate

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To a stirred solution of ethyl 4-aminobenzoate (5 gm, 30.3 mmol) under nitrogen atmosphere was added pyridine (50 ml) at 0° C. and stirred for 10 min. Quinoline-8-sulfonyl chloride 89 (8.94 gm, 39.4 mmol) was then added to the reaction mixture at the same temperature. The resulting mixture was stirred for 16 hr at RT. After completion of the reaction, the solvent was removed under low pressure. The traces of pyridine were removed by co-distillation with toluene. Diethylether was added to the resulting residue, and the solid product was filtered out and air-dried. The resulting crude product (8.0 gm, 74%) was taken to the next step without further purification.

Workup

  1. stirringThe resulting mixture was stirred for 16 hr at RT
  2. customAfter completion of the reaction
  3. customthe solvent was removed under low pressure
  4. customThe traces of pyridine were removed by co-distillation with toluene
  5. additionDiethylether was added to the resulting residue
  6. filtrationthe solid product was filtered out and
  7. customair-dried
  8. customThe resulting crude product (8.0 gm, 74%) was taken to the next step without further purification

Sources & evidence

ORD record
ord-29c0526d4c6140309f840f68b3b62a0f
Source dataset
uspto-grants-2014_07
Patent number
US08785450B2

Linked notes

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