Methyl Anthranilate → Methyl 2-(3-chloro-4-methoxybenzamido)benzoate

HRID 2099969노트

반응식

HRID 2099969 반응식
[NH2:1][C:2]1[CH:11]=[CH:10][CH:9]=[CH:8][C:3]=1[C:4]([O:6][CH3:7])=[O:5].[Cl:12][C:13]1[CH:14]=[C:15]([CH:19]=[CH:20][C:21]=1[O:22][CH3:23])[C:16](O)=[O:17].CCN=C=NCCCN(C)C>CN(C=O)C.CN(C1C=CN=CC=1)C>[Cl:12][C:13]1[CH:14]=[C:15]([CH:19]=[CH:20][C:21]=1[O:22][CH3:23])[C:16]([NH:1][C:2]1[CH:11]=[CH:10][CH:9]=[CH:8][C:3]=1[C:4]([O:6][CH3:7])=[O:5])=[O:17]

참가 물질

6

반응물 3

HCID 8635Methyl AnthranilateHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 1699823-Chloro-p-anisic acid

생성물 1

HCID 800035Methyl 2-(3-chloro-4-methoxybenzamido)benzoate수율 33.2%

시약·촉매·용매 2

HCID 142844-(Dimethylamino)pyridine촉매HCID 6228Dimethylformamide용매

실험 절차

A solution of methyl 2-aminobenzoate (500 mg, 3.3 mmol) (Aldrich Chemical Co., Milwaukee, Wis.) and 3-chloro-4-methoxybenzoic acid (645 mg, 3.3 mmol) (Lancaster Synthesis Ltd., Windham, N.H.) in DMF (20 mL) was treated with EDCI (1.3 g, 6.6 mmol) and DMAP (800 mg, 6.6 mmol) at room temperature. The reaction mixture was stirred for 24 hours, and then concentrated. The crude residue was dissolved in EtOAc (50 mL) and washed with 0.1 N HCl (2×20 mL), saturated aqueous NaHCO3 (2×20 mL). The organic layer was dried (Na2SO4), filtered, and concentrated. The crude product was purified by chromatography (SiO2, 15% EtOAc in hexanes) to afford 42A as a white solid (350 mg, 33%).

후처리

  1. concentrationconcentrated
  2. dissolutionThe crude residue was dissolved in EtOAc (50 mL)
  3. washwashed with 0.1 N HCl (2×20 mL), saturated aqueous NaHCO3 (2×20 mL)
  4. dry with materialThe organic layer was dried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe crude product was purified by chromatography (SiO2, 15% EtOAc in hexanes)

출처 및 근거

ORD 기록
ord-2ebb2b1e16f546d5ae3a5bb1b7b7de45
출처 데이터셋
uspto-grants-2009_08
특허 번호
US07569725B2

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