HCID 22646628, compound → HCID 22646645, compound

HRID 393671Notes

Reaction equation

[CH2:1]([O:8][C:9]1[CH:10]=[C:11]([CH:24]=[CH:25][C:26]=1[C:27]#[N:28])[NH:12][CH:13]=[C:14]1[C:19](=[O:20])OC(C)(C)OC1=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1>C1C=CC(C2C=CC=CC=2)=CC=1.C1C=CC(OC2C=CC=CC=2)=CC=1>[CH2:1]([O:8][C:9]1[CH:10]=[C:11]2[C:24]([C:19](=[O:20])[CH:14]=[CH:13][NH:12]2)=[CH:25][C:26]=1[C:27]#[N:28])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

Conditions

Temperature: 190 °C

Procedure

5-((3-Benzyloxy-4-cyanoanilino)methylene)-2,2-dimethyl-1,3-dioxane-4,6-dione (6 g, 15.9 mmol) was suspended in DOWTHERM A, (trade mark of Fluka Chemie AG), (100 ml) and heated to 190° C. The mixture was stirred for 1 hour at 190° C. Upon cooling to ambient temperature the product precipitated out. Ether (125 ml) was added and the suspension was stirred for 30 minutes. The product was collected by filtration, washed with ether and dried under vacuum to give 7-benzyloxy-6-cyano-1,4-dihydroquinolin-4-one (3.5 g) which was used without further purification in the next step.

Workup

temperatureUpon cooling to ambient temperature the product
customprecipitated out
additionEther (125 ml) was added
stirringthe suspension was stirred for 30 minutes
filtrationThe product was collected by filtration
washwashed with ether
customdried under vacuum

Sources & evidence

ORD record: ord-2229850ae7bf4a0890a12a752e82ddef
Source dataset: uspto-grants-2004_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06809097B1

Reaction notes

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