Dimethoxymethane → HCID 20188673, compound

HRID 1789606Notes

Reaction equation

[CH3:1][C:2]1[CH:11]=[CH:10][C:9]2[C:4](=[C:5]([N+:14]([O-:16])=[O:15])[CH:6]=[C:7]([O:12][CH3:13])[CH:8]=2)[N:3]=1.B(Br)(Br)Br.I.[CH3:22][O:23]COC>>[CH3:1][C:2]1[CH:11]=[CH:10][C:9]2[C:4](=[C:5]([N+:14]([O-:16])=[O:15])[CH:6]=[C:7]([O:12][CH2:13][O:23][CH3:22])[CH:8]=2)[N:3]=1

Participants

Reactant 4

HCID 8020Dimethoxymethane

HCID 24841Hydrogen iodide

HCID 25134Boron tribromide

HCID 2531416-Methoxy-2-methyl-8-nitroquinoline

Product 1

HCID 20188673HCID 20188673, compound

Procedure

The preparation of chelators where R8 and R9 are part of a quinoline ring and W=OH begins, for example, with 2-methyl-6-methoxy-8-nitroquinoline. The methoxy group could be cleaved with BBr3 or hot HI to yield a 6-hydroxy group, which could then be protected by reaction with dimethoxymethane under acid catalysis to yield 2-methyl-6-methoxymethyloxy-8-nitroquinoline. This can be used as starting material for the synthesis outlined above for 2-methyl-6-W-8-nitroquinoline, leading to chelators with W=OCH2OCH3. Mild acid hydrolysis of this compound gives chelators with W=OH.

Workup

customThe preparation of chelators where R8 and R9
customto yield a 6-hydroxy group, which

Sources & evidence

ORD record: ord-db8c3bfdb4b147168d544c9a87d5e659
Source dataset: uspto-grants-1987_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04689432

Reaction notes

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