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

HRID 7730

反応式

HRID 7730 の反応式
[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

参加物

6

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-f980798fac1b41878444490f8b753fdb
出典データセット
uspto-grants-2006_08
特許番号
US07087601B2

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