Methyl iodide → 5-Methoxy-2-nitrobenzaldehyde
Reaction equation
[OH:1][C:2]1[CH:3]=[CH:4][C:5]([N+:10]([O-:12])=[O:11])=[C:6]([CH:9]=1)[CH:7]=[O:8].IC.[C:15](=O)([O-])[O-].[K+].[K+]>CN(C=O)C>[CH3:15][O:1][C:2]1[CH:3]=[CH:4][C:5]([N+:10]([O-:12])=[O:11])=[C:6]([CH:9]=1)[CH:7]=[O:8]Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Procedure
In this scheme 5-hydroxy-2-nitrobenzaldehyde 1 is reacted in DMF with iodomethane and potassium carbonate to yield 5-methoxy-2-nitrobenzaldehyde 2. The methoxybenzaldehyde is heated with p-toluene sulfonic acid monohydrate (catalytic amount) in toluene to obtain the dioxane derivative 3, which is hydrogenated to give 2-(1,3-dioxolan-2yl)-4-methoxyphenylamine 4. Following conversion to the ethoxycarboxamide 5 and then to the formyl carboxamide 6,6-methoxyquinazolin-2-ol 7 is obtained by ring closure with ammonia. Reaction with phosphorus oxychloride then yields the desired 2-chloro-6-methoxyquinazoline intermediate 8.
Sources & evidence
- ORD record
- ord-7e5a270051744646abff8a6215d787d3
- Source dataset
- uspto-grants-2010_04
- Patent number
- US07691866B2
Reaction notes
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