Dimethylformamide → 9-Diethylaminoacetyl-6-nitro-1,4,7,8,9,10-hexahydro-pyrido[3,4-f]quinoxaline-2,3-dione

HRID 1739674Notes

Reaction equation

Cl.[CH2:2]([N:4]([CH2:9][CH3:10])[CH2:5][C:6]([OH:8])=O)[CH3:3].C(N1C=CN=C1)(N1C=CN=C1)=O.CN(C=O)C.[N+:28]([C:31]1[C:40]2[N:41]=[CH:42][CH:43]=[CH:44][C:39]=2[C:38]2[C:33](=[N:34][C:35](=[O:46])[C:36](=[O:45])[N:37]=2)[CH:32]=1)([O-:30])=[O:29]>C1COCC1.C(N(CC)CC)C>[CH2:9]([N:4]([CH2:5][C:6]([N:41]1[CH2:42][CH2:43][C:44]2[C:31]([N+:28]([O-:30])=[O:29])=[CH:32][C:33]3[NH:34][C:35](=[O:46])[C:36](=[O:45])[NH:37][C:38]=3[C:39]=2[CH2:40]1)=[O:8])[CH2:2][CH3:3])[CH3:10]

Participants

Conditions

Temperature: 80 °C

Procedure

A mixture of N,N-diethylglycine hydrochloride (96 mg, 0.57 mmol) and carbonyldiimidazole (92 mg, 0.57 mmol) in THF (5 mL) were refluxed under a nitrogen atmosphere for 15 min. With the bath temperature at 70° C., DMF (7 mL) and 6-nitro-pyridoquinoxalinedione (0.1 g, 0.38 mmol) were added, and finally triethylamine (265 μL) was added and the reaction heated for 14 h at 80° C. The solvent was removed and the residue triturated with water, collected by filtration and washed with diethyl ether. An orange brown solid (104 mg) was obtained in 73% yield, mp 285-290° C. (dec); m/e M+1 376, nmR, IR.

Workup

temperaturewere refluxed under a nitrogen atmosphere for 15 min
customThe solvent was removed
customthe residue triturated with water
filtrationcollected by filtration
washwashed with diethyl ether

Sources & evidence

ORD record: ord-0ce50a76897942f6bb210cff86eabd18
Source dataset: uspto-grants-1999_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05968928

Reaction notes

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