Pyridine → HCID 13816784, compound

HRID 847431Notes

Reaction equation

[CH2:1]([O:3][C:4]([C:6]1[C:7](=[O:23])[C:8]2[CH:9]=[C:10]([F:22])[C:11]([F:21])=[C:12]3[O:17][CH2:16][CH:15]([CH2:18][OH:19])[N:14]([CH:20]=1)[C:13]=23)=[O:5])[CH3:2].N1C=CC=CC=1.[N+:30]([C:33]1[CH:34]=[C:35]([CH:39]=[C:40]([N+:42]([O-:44])=[O:43])[CH:41]=1)[C:36](Cl)=[O:37])([O-:32])=[O:31]>O1CCCC1>[CH2:1]([O:3][C:4]([C:6]1[C:7](=[O:23])[C:8]2[CH:9]=[C:10]([F:22])[C:11]([F:21])=[C:12]3[O:17][CH2:16][CH:15]([CH2:18][O:19][C:36](=[O:37])[C:35]4[CH:34]=[C:33]([N+:30]([O-:32])=[O:31])[CH:41]=[C:40]([N+:42]([O-:44])=[O:43])[CH:39]=4)[N:14]([CH:20]=1)[C:13]=23)=[O:5])[CH3:2]

Participants

Conditions

Temperature: 90 °C

Procedure

One gram of (±)-9,10-difluoro-3-hydroxymethyl-7-oxo-2,3-dihydro-7H-pyrido[1,2,3-de][1,4]benzoxazine-6-carboxylic acid ethyl ester (I) and 500 mg of pyridine were suspended in 100 ml of anhydrous tetrahydrofuran (THF), and 1.6 g of 3,5-dinitrobenzoyl chloride was added thereto, followed by refluxing at 90° C. The suspension was once dissolved, and a colorless precipitate was then formed. The reaction was continued for 1.5 hours. After cooling, the precipitate was collected by filtration, washed with methanol and diethyl ether and dried to obtain 1.2 g of (±)-9,10-difluoro-3-(3,5-dinitrobenzoyloxy)methyl-7-oxo-2,3-dihydro-7H-pyrido[1,2,3-de][1,4]benzoxazine-6-carboxylic acid ethyl ester (II) as a colorless powder having a melting point of 240°-242° C.

Workup

dissolutionThe suspension was once dissolved
customa colorless precipitate was then formed
temperatureAfter cooling
filtrationthe precipitate was collected by filtration
washwashed with methanol and diethyl ether
customdried

Sources & evidence

ORD record: ord-be17a084cb3c4fccaa1786614f0166ef
Source dataset: uspto-grants-1992_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05142046

Reaction notes

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