Dimethylformamide → 5,7-diethyl-1-(4-nitrobenzyl)-1,6-naphthyridin-2(1H)-one

HRID 487408Notes

Reaction equation

S(Cl)(Cl)=O.Br[C:6]1[CH:14]=[CH:13][CH:12]=[CH:11][C:7]=1C(O)=O.[N+:15]([C:18]1[CH:24]=[CH:23][C:21](N)=[CH:20][CH:19]=1)([O-:17])=[O:16].[CH3:25][N:26]([CH:28]=[O:29])[CH3:27]>C1(C)C=CC=CC=1.CN1CCCC1=O>[CH2:14]([C:13]1[N:15]=[C:18]([CH2:24][CH3:23])[CH:19]=[C:25]2[C:12]=1[CH:11]=[CH:7][C:28](=[O:29])[N:26]2[CH2:27][C:21]1[CH:23]=[CH:24][C:18]([N+:15]([O-:17])=[O:16])=[CH:19][CH:20]=1)[CH3:6]

Participants

Conditions

Temperature: 80 °C

Procedure

Thionyl chloride (120.5 g) was added to a stirred mixture of 2-bromobenzoic acid (194 g) in toluene (500 ml) and DMF (5 ml) and the mixture was heated at 80° C. for 4 hours. The solution was cooled to 20° C. and added slowly to a solution of 4-nitroaniline (133.1 g) in toluene (500 ml) and N-methylpyrrolidone (NMP) (120 ml), maintaining the temperature of the reaction mixture between 20°-25° C. The reaction mixture was then stirred for 24 hours when a solid precipitated. Water (360 ml) was added with rigorous stirring and the suspended solid was collected by filtration and washed successively with water, toluene and acetonitrile to give 2-bromo-N-(4-nitrophenyl)benzamide (B) as a solid, in 87% yield; m.p. 200°-202° C.; NMR (d6 -DMSO): 7.4-7.8(m, 7H), 8.0(d, 2H), 8.3(d, 2H), 11.5(brs, 1H); which was used without further purification.

Workup

temperatureThe solution was cooled to 20° C.
temperaturemaintaining the temperature of the reaction mixture between 20°-25° C
customprecipitated
additionWater (360 ml) was added
stirringwith rigorous stirring
filtrationthe suspended solid was collected by filtration
washwashed successively with water, toluene and acetonitrile

Sources & evidence

ORD record: ord-c766c60df76d4f809c51f7ff2829c0b9
Source dataset: uspto-grants-1994_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05294620

Reaction notes

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