Pyridine → HCID 13816784, compound

HRID 704058Notes

Reaction equation

HRID 704058 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

5

Reactant 3

HCID 1049PyridineHCID 74323,5-Dinitrobenzoyl chlorideHCID 13309007HCID 13309007, compound

Product 1

HCID 13816784HCID 13816784, compoundYield 75.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

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. NMR (CDCl3 /5% DMSO-d6) δ(ppm); 1,30 (3H, t, J=7.0 Hz, --CH2CH3), 4.26 (2H, q, J=7.0 Hz, --CH2CH3), 4.4-4.5 (5H, m), 7.76 (1H, dd, J=11.0 Hz, 7.0 Hz, C8 -H), 8.8 (1H, s, C5 -H), 9.0 (2H, d, J=3.0 Hz, aromatic ring proton) and 9.2 (1H, t, J=3.0 Hz, aromatic ring proton).

Workup

  1. dissolutionThe suspension was once dissolved
  2. customa colorless precipitate was then formed
  3. temperatureAfter cooling
  4. filtrationthe precipitate was collected by filtration
  5. washwashed with methanol and diethyl ether
  6. customdried

Sources & evidence

ORD record
ord-67a1b586316c4616a08b0a07e246c935
Source dataset
uspto-grants-1991_01
Patent number
US04985557

Reaction notes

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