Acetic Acid → HCID 58154538, compound

HRID 2359423Notes

Reaction equation

HRID 2359423 reaction equation
[NH2:1][C:2]1[C:11]([CH2:12][NH2:13])=[CH:10][CH:9]=[CH:8][C:3]=1[C:4]([O:6][CH3:7])=[O:5].[CH:14](=O)[C:15]1[CH:20]=[CH:19][CH:18]=[N:17][CH:16]=1.C(O)(=O)C>O1CCOCC1>[N:17]1[CH:18]=[CH:19][CH:20]=[C:15]([CH:14]2[NH:13][CH2:12][C:11]3[C:2](=[C:3]([C:4]([O:6][CH3:7])=[O:5])[CH:8]=[CH:9][CH:10]=3)[NH:1]2)[CH:16]=1

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 103713-PyridinecarboxaldehydeHCID 58154533HCID 58154533, compound

Product 1

HCID 58154538HCID 58154538, compoundYield 53.6%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A mixture of methyl 2-amino-3-(aminomethyl)benzoate (5.0 g, 27.7 mmol), nicotinaldehyde (3.0 g, 27.7 mmol) and acetic acid (2.0 mL) in dioxane (50 mL) was stirred in the microwave for 20 minutes. The solvent was removed in vacuo and the residue was purified by chromatography on silica gel (10% methanol in CH2Cl2) to give methyl 2-(pyridin-3-yl)-1,2,3,4-tetrahydroquinazoline-8-carboxylate (4.0 g, 53% yield).

Workup

  1. customThe solvent was removed in vacuo
  2. customthe residue was purified by chromatography on silica gel (10% methanol in CH2Cl2)

Sources & evidence

ORD record
ord-fc2aa6238e6f43419d0e6d6d1f9a5a6c
Source dataset
uspto-grants-2014_04
Patent number
US08685970B2

Reaction notes

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