Triethylamine → Phenyl quinolin-4-ylcarbamate

HRID 571986Notes

Reaction equation

HRID 571986 reaction equation
[N:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1NC(=O)OC1C=CC=CC=1.C([N:23](CC)CC)C.Cl[C:29]([O:31][C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1)=[O:30]>ClCCl>[N:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[C:4]([NH:23][C:29](=[O:30])[O:31][C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=2)=[CH:3][CH:2]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 15891Phenyl chloroformateHCID 54327762Phenyl quinolin-2-ylcarbamate

Product 1

HCID 86676323Phenyl quinolin-4-ylcarbamate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Quinolin-4-amine (A) (76 mg, 0.53 mmol) was dissolved in dichloromethane. To the reaction mixture was added triethylamine (0.09 mL, 0.63 mmol) and phenyl chloroformate (0.07 mL, 0.55 mmol) and stirred at room temperature for 1 h. The reaction mixture was concentrated under reduced pressure to afford the crude phenyl quinolin-4-ylcarbamate which was directly used for next step without purification.

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure

Sources & evidence

ORD record
ord-d3468b510e014d31bb5fa509dc369369
Source dataset
uspto-grants-2015_05
Patent number
US09029378B2

Reaction notes

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