Ethyl orthoformate → HCID 21075817, compound

HRID 1373942Notes

Reaction equation

HRID 1373942 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.[CH:21](OCC)(OCC)OCC.Cl.N1C=CC=CC=1>C1(C)C=CC=CC=1.C(Cl)(Cl)Cl>[N:12]1([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]=[CH:21]1

Participants

6

Reactant 3

HCID 31214Ethyl orthoformateHCID 10176127Pyridinium chlorideHCID 21075823tert-butyl N'-(3-aminoquinolin-4-yl)hydrazinecarboxylate

Product 1

HCID 21075817HCID 21075817, compound

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 6212ChloroformSolvent

Conditions

Temperature
130 °C

Procedure

A suspension of tert-butyl N′-(3-aminoquinolin-4-yl)hydrazinecarboxylate (6.50 g, 23.7 mmol) in 100 mL of toluene was treated with triethyl orthoformate (8.68 mL, 52.2 mmol) and pyridine hydrochloride (0.14 g, 1.2 mmol) and heated to 130° C. under an atmosphere of nitrogen. After 23 h, the reaction mixture was concentrated under reduced pressure to yield a red/brown oil. The oil was dissolved in CHCl3 (150 mL) and washed with water (2×50 mL), brine (50 mL), dried over Na2SO4, filtered and concentrated under reduced pressure to yield 6.74 of tert-butyl N-(1H-imidazo[4,5-c]quinolin-1-yl)carbamate as a red/orange oil.

Workup

  1. concentrationthe reaction mixture was concentrated under reduced pressure
  2. customto yield a red/brown oil
  3. washwashed with water (2×50 mL), brine (50 mL)
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-5c6c6be9471f4593a8dde2100a61d5db
Source dataset
uspto-grants-2007_01
Patent number
US07163947B2

Reaction notes

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