Potassium Carbonate → HCID 21280642, compound

HRID 414427Notes

Reaction equation

[I-].[CH3:2][O:3][CH2:4][CH:5]1[NH+:9]([CH3:10])[C:8]([CH3:12])([CH3:11])[CH2:7][O:6]1.C(=O)([O-])[O-].[K+].[K+].[N:19]([C:21]1[C:30]([OH:31])=[CH:29][CH:28]=[C:27]2[C:22]=1[CH:23]=[CH:24][CH:25]=[N:26]2)=O>C1C=CC=CC=1>[CH3:2][O:3][C:4]1[C:5]2([N:9]([CH3:10])[C:8]([CH3:12])([CH3:11])[CH2:7][O:6]2)[O:31][C:30]2[CH:29]=[CH:28][C:27]3[N:26]=[CH:25][CH:24]=[CH:23][C:22]=3[C:21]=2[N:19]=1

Participants

Conditions

Temperature: 70 °C

Procedure

Into a dry 250 ml three-necked flask kept under dry nitrogen and fitted with a reflux condenser and internal thermometer was added 2-methoxymethyl-3,4,4-trimethyl-1,3-oxazolidinium iodide (7.13 grams, 25 mmole), powdered potassium carbonate (8.97 grams, 65 mmole) and 125 ml dry benzene. The heterogeneous mixture was heated at 70° C. for 90 minutes before addition of 5-nitroso-6-quinolinol (5.44 grams, 25 mmole). The resulting reaction mixture was heated at 70° C. for 17 hours, cooled and filtered through Celite® diatomaceous earth powder. The solvent was removed in vacuo from the filtrate, and the resulting residue purified by flash chromatography to yield 0.33 grams of 2'-methoxy-3,4,4-trimethylspiro [oxazolidine-2,3'-[3H] pyrido [3,2-f] [1,4] benzoxazine].

Workup

customInto a dry 250 ml three-necked flask kept under dry nitrogen
customfitted with a reflux condenser
customThe resulting reaction mixture
temperaturecooled
filtrationfiltered through Celite® diatomaceous earth powder
customThe solvent was removed in vacuo from the filtrate
customthe resulting residue purified by flash chromatography

Sources & evidence

ORD record: ord-379e45dec7dc4adda77bbbda6d8d78dc
Source dataset: uspto-grants-1988_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04792224

Reaction notes

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