Trimethyl orthoacetate → HCID 21075820, compound

HRID 1373892Notes

Reaction equation

HRID 1373892 reaction equation
[NH2:1][C:2]1[CH:3]=[N:4][C:5]2[C:10]([C:11]=1[NH:12][NH:13][C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])=[CH:9][CH:8]=[CH:7][CH:6]=2.[C:21](OC)(OC)(OC)[CH3:22].CO.CCOC(C)=O>C1(C)C=CC=CC=1.Cl.N1C=CC=CC=1>[CH3:21][C:22]1[N:12]([NH:13][C:14](=[O:15])[O:16][C:17]([CH3:20])([CH3:19])[CH3:18])[C:11]2[C:10]3[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=3[N:4]=[CH:3][C:2]=2[N:1]=1

Participants

6

Reactant 3

HCID 15050Trimethyl orthoacetateHCID 21075823tert-butyl N'-(3-aminoquinolin-4-yl)hydrazinecarboxylateHCID 21584119Ethylacetate methanol

Product 1

HCID 21075820HCID 21075820, compoundYield 84.4%

Reagents, catalysts & solvents 2

HCID 10176127Pyridinium chlorideCatalystHCID 1140TolueneSolvent

Procedure

A solution of tert-butyl N′-(3-aminoquinolin-4-yl)hydrazinecarboxylate (11.67 g, 42.5 mmol) in 400 mL of anhydrous toluene was treated with trimethyl orthoacetate (5.96 mL, 46.8 mmol) and pyridine hydrochloride (100 mg) under an atmosphere of N2 and heated to reflux. After stirring for 3 h, the reaction mixture was concentrated under reduced pressure to give a red solid. Chromatography (SiO2, 0–10% MeOH/EtOAc) gave tert-butyl N-(2-methyl-1H-imidazo[4,5-c]quinolin-1-yl)carbamate (10.7 g) as a yellow foam.

Workup

  1. temperatureheated to reflux
  2. concentrationthe reaction mixture was concentrated under reduced pressure
  3. customto give a red solid

Sources & evidence

ORD record
ord-4698ee159fcf4389a15ee02da25f4d4c
Source dataset
uspto-grants-2007_01
Patent number
US07163947B2

Reaction notes

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