Sodium Hydroxide → 4-Methoxy-3-methyl-2-[(5-methyl-pyridine-2-carbonyl)-amino]-benzoic acid methyl ester

HRID 1443472

반응식

HRID 1443472 반응식
[CH3:1][O:2][C:3](=[O:14])[C:4]1[CH:9]=[CH:8][C:7]([O:10][CH3:11])=[C:6]([CH3:12])[C:5]=1[NH2:13].[CH3:15][C:16]1[CH:17]=[CH:18][C:19]([C:22](O)=[O:23])=[N:20][CH:21]=1.P(Cl)(Cl)(Cl)=O.[OH-].[Na+]>ClCCl.N1C=CC=CC=1>[CH3:1][O:2][C:3](=[O:14])[C:4]1[CH:9]=[CH:8][C:7]([O:10][CH3:11])=[C:6]([CH3:12])[C:5]=1[NH:13][C:22]([C:19]1[CH:18]=[CH:17][C:16]([CH3:15])=[CH:21][N:20]=1)=[O:23]

참가 물질

7

반응물 4

HCID 14798Sodium HydroxideHCID 24813Phosphorus oxychlorideHCID 1995755-Methylpicolinic acidHCID 59165444Methyl 2-amino-4-methoxy-3-methylbenzoate

생성물 1

HCID 576872244-Methoxy-3-methyl-2-[(5-methyl-pyridine-2-carbonyl)-amino]-benzoic acid methyl ester수율 65.2%

시약·촉매·용매 2

HCID 1049Pyridine용매HCID 6344Dichloromethane용매

실험 절차

2-Amino-4-methoxy-3-methyl-benzoic acid methyl ester (400 mg, 2 mmol) and 5-methyl-pyridine-2-carboxylic acid (280 mmol, 2 mmol) where dissolved in dichloro-methane (8 ml) and pyridine (1 ml). Phosphorous oxychloride (0.37 ml) was added while cooling on ice-bath. The mixture was left at 0° C. for 1 h then allowed to attain room temperature. Aqueous sodium hydroxide (20 ml, 1M) was added and the mixture were extracted with dichloromethane. Purification by column chromatography on silica gel (ether-pentane 1:1) gave pure title compound (410 mg, 65%). MS (M−H)+ 315.1

후처리

  1. temperaturewhile cooling on ice-bath
  2. customto attain room temperature
  3. extractionthe mixture were extracted with dichloromethane
  4. customPurification by column chromatography on silica gel (ether-pentane 1:1)

출처 및 근거

ORD 기록
ord-b88460349c4342418e3e686e5aa8d14c
출처 데이터셋
uspto-grants-2010_02
특허 번호
US07659245B2

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