Pyridine → ethyl 2-{[(2-nitrophenyl)carbonyl]amino}benzoate

HRID 881577노트

반응식

HRID 881577 반응식
[N+:1]([C:4]1[CH:12]=[CH:11][CH:10]=[CH:9][C:5]=1[C:6]([OH:8])=O)([O-:3])=[O:2].C(Cl)(=O)C(Cl)=O.[NH2:19][C:20]1[CH:30]=[CH:29][CH:28]=[CH:27][C:21]=1[C:22]([O:24][CH2:25][CH3:26])=[O:23].N1C=CC=CC=1>ClCCCl.C(Cl)Cl.CN(C=O)C>[N+:1]([C:4]1[CH:12]=[CH:11][CH:10]=[CH:9][C:5]=1[C:6]([NH:19][C:20]1[CH:30]=[CH:29][CH:28]=[CH:27][C:21]=1[C:22]([O:24][CH2:25][CH3:26])=[O:23])=[O:8])([O-:3])=[O:2]

참가 물질

8

반응물 4

HCID 1049PyridineHCID 6877Ethyl 2-aminobenzoateHCID 110872-Nitrobenzoic acidHCID 65578Oxalyl chloride

생성물 1

HCID 710775ethyl 2-{[(2-nitrophenyl)carbonyl]amino}benzoate

시약·촉매·용매 3

HCID 111,2-Dichloroethane용매2회HCID 6228Dimethylformamide용매HCID 6344Dichloromethane용매

실험 절차

A catalytic amount of DMF was added to a stirred solution of 2-nitrobenzoic acid (2.30 g, 13.8 mmol) and oxalyl chloride (6.0 mL, 69 mmol) in 1,2-dichloroethane (70 mL) at r.t. and under nitrogen flow. After 1 h, the reaction was concentrated, re-dissolved in 1,2-dichloroethane and concentrated again. The crude was immediately dissolved in 1,2-dichloroethane (25 mL) before ethyl 2-aminobenzoate (1.00 mL, 6.76 mmol) and pyridine (1.70 mL, 21.0 mmol) was added. The reaction was stirred 45 min at r.t. and under nitrogen atmosphere before being diluted with DCM and washed with HCl (aq., 1M), NaHCO3 (aq., sat., 2×) and brine. The organic phase was dried over Na2SO4, filtered, and concentrated. The crude was purified by column chromatography (SiO2, toluene:acetone 100:0→98:2) to give compound 20 in quant yield (2.24 g).

후처리

  1. concentrationthe reaction was concentrated
  2. dissolutionre-dissolved in 1,2-dichloroethane
  3. concentrationconcentrated again
  4. additionwas added
  5. washwashed with HCl (aq., 1M), NaHCO3 (aq., sat., 2×) and brine
  6. dry with materialThe organic phase was dried over Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customThe crude was purified by column chromatography (SiO2, toluene:acetone 100:0→98:2)

출처 및 근거

ORD 기록
ord-ebf66eca340e4cd2b48bab055247977c
출처 데이터셋
uspto-grants-2015_03
특허 번호
US08993622B2

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