Triethylamine → 2-Hydroxy-N-methoxy-N-methyl-[1,1'-biphenyl]-3-carboxamide

HRID 983802

반응식

HRID 983802 반응식
[OH:1][C:2]1[C:10]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)=[CH:9][CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=O.C(Cl)(=O)C(Cl)=O.Cl.[CH3:24][NH:25][O:26][CH3:27].C(N(CC)CC)C>CCOC(C)=O.CN(C=O)C.C(Cl)Cl>[CH3:27][O:26][N:25]([CH3:24])[C:4](=[O:6])[C:3]1[CH:7]=[CH:8][CH:9]=[C:10]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[C:2]=1[OH:1]

참가 물질

8

반응물 4

HCID 8471TriethylamineHCID 93483-Phenylsalicylic acidHCID 65578Oxalyl chlorideHCID 81138Methanamine, N-methoxy-, hydrochloride (1:1)

생성물 1

HCID 110543102-Hydroxy-N-methoxy-N-methyl-[1,1'-biphenyl]-3-carboxamide수율 30.3%

시약·촉매·용매 3

HCID 6228Dimethylformamide촉매HCID 6344Dichloromethane용매HCID 8857Ethyl Acetate용매

실험 절차

2-hydroxy-3-phenylbenzoic acid (218, 3.0 g, 14 mmol) is dissolved in EtOAc (50 ml) and a few drops of DMF are added. Oxalyl chloride (2.5 ml, 1.5 eq) is added and the reaction is stirred under a dry atmosphere for 1 h. The reaction mixture is then concentrated in vacuo to yield a mixture of clear oil and white solid. This mixture is diluted with CH2Cl2 (50 ml) followed by the addition of N,O-dimethyl hydroxylamine hydrochloride (1.5 g, 1.1 eq) and triethylamine (3.9 ml, 2 eq). This mixture is stirred for 12-18 h under a dry atmosphere. Dilution of the reaction mixture with EtOAc and subsequent washing with dilute HCl and brine, followed by drying (MgSO4) and concentration in vacuo yields a mixture of reaction products. Flash chromatography (20/80 EtOAc/Hexanes) afforded N-methoxy-N-methyl-2-hydroxy-3-phenylbenzamide (219, 1.09 g) as a white solid.

후처리

  1. concentrationThe reaction mixture is then concentrated in vacuo
  2. customto yield
  3. additiona mixture of clear oil and white solid
  4. stirringThis mixture is stirred for 12-18 h under a dry atmosphere
  5. washDilution of the reaction mixture with EtOAc and subsequent washing with dilute HCl and brine
  6. customby drying
  7. concentration(MgSO4) and concentration in vacuo
  8. customyields
  9. additiona mixture of reaction products

출처 및 근거

ORD 기록
ord-f276e7c9ffd34ec0ada420ba79622291
출처 데이터셋
uspto-grants-2005_03
특허 번호
US06867200B1

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