Dimethylformamide → HCID 87235355, 화합물

HRID 2194495노트

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HRID 2194495 반응식
[O:1]=[C:2]1[C:11]([C:12](O)=[O:13])=[CH:10][C:9]2[C:4](=[N:5][CH:6]=[CH:7][CH:8]=2)[N:3]1[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.C(Cl)(=O)C([Cl:24])=O.CN(C)C=O>ClCCl>[O:1]=[C:2]1[C:11]([C:12]([Cl:24])=[O:13])=[CH:10][C:9]2[C:4](=[N:5][CH:6]=[CH:7][CH:8]=2)[N:3]1[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

참가 물질

5

반응물 3

HCID 6228DimethylformamideHCID 65578Oxalyl chlorideHCID 534020662-Oxo-1-phenyl-1,2-dihydro-1,8-naphthyridine-3-carboxylic acid

생성물 1

HCID 87235355HCID 87235355, 화합물

시약·촉매·용매 1

HCID 6344Dichloromethane용매

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온도
40 °C

실험 절차

1.62 g (6.1 mmol) of 2-oxo-1-phenyl-1,2-dihydro-1,8-naphthyridine-3-carboxylic acid was dissolved in dichloromethane (60 mL), and 3.7 mL (44 mmol) of oxalyl chloride was added thereto. One droplet of N,N-dimethylformamide was added to the above mixture, and the resulting mixture was stirred for one hour at 40° C. The reaction mixture was concentrated under reduced pressure, and thus 2-oxo-1-phenyl-1,2-dihydro-1,8-naphthyridine-3-carboxylic acid chloride was obtained. The acid chloride thus obtained was dissolved in dichloromethane (60 mL), and 0.75 g (6.7 mmol) of 1,3-cyclohexanedione and 1.03 mL (7.3 mmol) of triethylamine were added to the above solution. The resulting mixture was stirred for 2 hours at room temperature. The reaction mixture was poured into an aqueous solution of sodium hydrogen carbonate, and the mixture was extracted with dichloromethane. The organic phase was dried and concentrated. The residue was washed with diisopropyl ether, and thus 2.16 g (yield: 99%) of the title compound was obtained as a light yellow solid.

후처리

  1. concentrationThe reaction mixture was concentrated under reduced pressure

출처 및 근거

ORD 기록
ord-073521c806cd49998d2b3df577726de9
출처 데이터셋
uspto-grants-2012_12
특허 번호
US08334236B2

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