4-Chloro-3-nitrobenzaldehyde → 4-(4-chloro-3-nitrophenyl)-1-methyl-4,9-dihydro-1H-isoxazolo [3,4-b]pyrano[4,3-e]pyridine-3,5(6H,8H)-dione

HRID 1862454Notes

Reaction equation

HRID 1862454 reaction equation
[NH2:1][C:2]1[N:3]([CH3:8])[O:4][C:5](=[O:7])[CH:6]=1.[N+:9]([C:12]1[CH:13]=[C:14]([CH:17]=[CH:18][C:19]=1[Cl:20])[CH:15]=O)([O-:11])=[O:10].[O:21]1[CH2:26][C:25](=O)[CH2:24][C:23](=[O:28])[CH2:22]1>C(O)C>[Cl:20][C:19]1[CH:18]=[CH:17][C:14]([CH:15]2[C:24]3[C:23](=[O:28])[CH2:22][O:21][CH2:26][C:25]=3[NH:1][C:2]3[N:3]([CH3:8])[O:4][C:5](=[O:7])[C:6]2=3)=[CH:13][C:12]=1[N+:9]([O-:11])=[O:10]

Participants

5

Reactant 3

HCID 855054-Chloro-3-nitrobenzaldehydeHCID 3252872H-pyran-3,5(4H,6H)-dioneHCID 234974983-Amino-2-methyl-2,5-dihydro-1,2-oxazol-5-one

Product 1

HCID 101996184-(4-chloro-3-nitrophenyl)-1-methyl-4,9-dihydro-1H-isoxazolo [3,4-b]pyrano[4,3-e]pyridine-3,5(6H,8H)-dione

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

The product from Example 45A (0.085 g, 0.75 mmol), 3nitro-4-chlorobenzaldehyde(0.14 g, 0.75 mmol) and 2H-pyran-3,5(4H,6H)-dione (0.085 g, 0.75 mmol) were heated in 2 mL of ethanol for 2 days. The resulting mixture was allowed to cool to ambient temperature and filtered to provide the title compound as the filter cake (0.09 g). 1H NMR (300 MHz, DMSO-d6) δ 3.28 (s, 3H), 4.06 (s, 2H), 4.58 (s, 2H), 4.88 (s, 1H), 7.6 (dd, 1H), 7.7 (d, 1H), 7.9 (d, 1H), 10.8 (s, 1H); MS (ESI) m/z 376 (M−H)−; Anal. Calcd for C16H12N3ClO6: C, 50.88;H, 3.20; N, 11.12. Found: C, 50.86;H, 3.63; N, 10.52.

Workup

  1. filtrationfiltered

Sources & evidence

ORD record
ord-4eb2152a71eb4e1fa5638ae6a96ee83c
Source dataset
uspto-grants-2003_03
Patent number
US06538004B2

Reaction notes

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