Methyl 2-(benzyloxy)-4-(((2,2-dimethyl-4,6-dioxo-1,3-dioxan-5-ylidene)methyl)amino)benzoate → Methyl 7-(benzyloxy)-4-oxo-1,4-dihydro-6-quinolinecarboxylate

HRID 853440Notes

Reaction equation

[CH2:1]([O:8][C:9]1[CH:18]=[C:17]([NH:19][CH:20]=[C:21]2[C:26](=[O:27])OC(C)(C)OC2=O)[CH:16]=[CH:15][C:10]=1[C:11]([O:13][CH3:14])=[O:12])[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:18]=[C:17]2[C:16]([C:26](=[O:27])[CH:21]=[CH:20][NH:19]2)=[CH:15][C:10]=1[C:11]([O:13][CH3:14])=[O:12])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

Conditions

Temperature: 200 °C

Procedure

After adding Dowtherm A (160 ml) to methyl 2-(benzyloxy)-4-(((2,2-dimethyl-4,6-dioxo-1,3-dioxan-5-ylidene)methyl)amino)benzoate (15.477 g, 37.6 mmol), the mixture was stirred at 200° C. for 1 hour. Upon cooling to room temperature, the precipitated crystals were filtered, washed with diethyl ether and blow-dried to obtain the title compound (7.19 g, 23.2 mmol, 61.8%).

Workup

temperatureUpon cooling to room temperature
filtrationthe precipitated crystals were filtered
washwashed with diethyl ether
customblow-dried

Sources & evidence

ORD record: ord-fb00f05103a9414882e1d473aefd51db
Source dataset: uspto-grants-2007_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07253286B2

Reaction notes

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