2-Aminophenol → N-(2-Hydroxyphenyl)-3-methoxy-4-methylbenzamide

HRID 7730

반응식

HRID 7730 반응식
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:9]=[CH:10][C:11]=1[CH3:12])[C:6]([OH:8])=O.S(Cl)(Cl)=O.[NH2:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=1[OH:24].C(N(C(C)C)CC)(C)C>C1COCC1>[OH:24][C:19]1[CH:20]=[CH:21][CH:22]=[CH:23][C:18]=1[NH:17][C:6](=[O:8])[C:5]1[CH:9]=[CH:10][C:11]([CH3:12])=[C:3]([O:2][CH3:1])[CH:4]=1

참가 물질

6

반응물 4

HCID 58012-AminophenolHCID 24386Thionyl ChlorideHCID 81531DiisopropylethylamineHCID 815794-Methyl-m-anisic acid

생성물 1

HCID 16378794N-(2-Hydroxyphenyl)-3-methoxy-4-methylbenzamide

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

3-Methoxy-4-methyl benzoic acid (1.2 g, 7.2 mmol) and thionyl chloride (10 mL) was heated to reflux conditions under argon until no starting material was observed by TLC. After cooling mixture to rt and concentration in vacuo, the resulting brown oil was dissolved in THF (15 mL) and slowly added to a cooled mixture of 2-aminophenol (780 mg, 7.1 mmol), diisopropylethyl amine (1.5 mL, 8.6 mmol) and THF (20 mL) at 0° C. Reaction mixture was allowed to warm to rt. After one hour, no starting material acid was observed by TLC. After concentrating reaction mixture in vacuo, the resulting brown oil was purified by flash chromatography on silica gel, using 1:4 EtOAc:hexanes. This afforded the desired intermediate, N-(2-hydroxyphenyl)-3-methoxy-4-methylbenzamide, as a yellow solid.

후처리

  1. temperatureto reflux conditions under argon until no starting material
  2. concentrationconcentration in vacuo
  3. dissolutionthe resulting brown oil was dissolved in THF (15 mL)
  4. customReaction mixture
  5. temperatureto warm to rt
  6. concentrationAfter concentrating
  7. customreaction mixture in vacuo
  8. customthe resulting brown oil was purified by flash chromatography on silica gel

출처 및 근거

ORD 기록
ord-f980798fac1b41878444490f8b753fdb
출처 데이터셋
uspto-grants-2006_08
특허 번호
US07087601B2

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