Phosphorus oxychloride → Ethyl 4-chloro-7-methyl-1,8-naphthyridine-3-carboxylate

HRID 2358555Notes

Reaction equation

[CH2:1]([O:3][C:4]([C:6]1[C:15](=O)[C:14]2[C:9](=[N:10][C:11]([CH3:17])=[CH:12][CH:13]=2)[NH:8][CH:7]=1)=[O:5])[CH3:2].O=P(Cl)(Cl)[Cl:20]>>[CH2:1]([O:3][C:4]([C:6]1[CH:7]=[N:8][C:9]2[C:14]([C:15]=1[Cl:20])=[CH:13][CH:12]=[C:11]([CH3:17])[N:10]=2)=[O:5])[CH3:2]

Participants

Reactant 2

HCID 24813Phosphorus oxychloride

HCID 5373687Ethyl 7-methyl-4-oxo-1,8-naphthyridine-3-carboxylate

Product 1

HCID 10562672Ethyl 4-chloro-7-methyl-1,8-naphthyridine-3-carboxylateYield 57%

Procedure

The product from Example 1b (1.0 g, 4.30 mmol) was reacted with 12 mL of POCl3 for 4 h following the procedure from Example 1d giving the title compound as a brownish-pink solid (619 mg, 57%).

Sources & evidence

ORD record: ord-82c919db49a4466dab28e83fcedb7654
Source dataset: uspto-grants-2010_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07763731B2

Reaction notes

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