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

HRID 881577ノート

反応式

HRID 881577 の反応式
[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]

参加物

8

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 3

HCID 111,2-Dichloroethane溶媒2 回HCID 6228Dimethylformamide溶媒HCID 6344Dichloromethane溶媒

実験手順

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).

後処理

  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)

出典と根拠

ORDレコード
ord-ebf66eca340e4cd2b48bab055247977c
出典データセット
uspto-grants-2015_03
特許番号
US08993622B2

反応ノート

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