Dimethyl Sulfoxide → Benzoic acid, 2-amino-6-methyl-, methyl ester

HRID 864712

反応式

HRID 864712 の反応式
[OH-].[K+].CS(C)=O.[CH3:7][C:8]1[CH:9]=[CH:10][CH:11]=[C:12]([NH2:17])[C:13]=1[C:14]([OH:16])=[O:15].I[CH3:19]>CCOCC>[CH3:7][C:8]1[CH:9]=[CH:10][CH:11]=[C:12]([NH2:17])[C:13]=1[C:14]([O:16][CH3:19])=[O:15]

参加物

6

反応物 4

HCID 679Dimethyl SulfoxideHCID 6328Methyl iodideHCID 14797Potassium HydroxideHCID 1512106-Methylanthranilic acid

生成物 1

HCID 583916Benzoic acid, 2-amino-6-methyl-, methyl ester収率 39%

試薬・触媒・溶媒 1

HCID 3283Diethyl Ether溶媒

実験手順

Powdered potassium hydroxide (7.4 g, 0.132 mol) was admixed with dimethyl sulfoxide (DMSO) (100 ml), and the mixture was stirred for 5 minutes. 6-Methylanthranilic acid (10.0 g, 0.066 mol) was then added to the mixture and iodomethane (4.52 ml, 0.073 mol) added dropwise. The reaction mixture was stirred for 30 minutes at room temperature, then diluted with 250 ml of ether, washed with water (3×100 ml), dried over magnesium sulfate and concentrated. The crude product was filtered through a pad of flash grade (32-63) silica gel and eluted with 1:9 ether:hexane to afford 4.23 g (39%) of methyl 6-methylanthranilate as an oil.

後処理

  1. additionadded dropwise
  2. stirringThe reaction mixture was stirred for 30 minutes at room temperature
  3. washwashed with water (3×100 ml)
  4. dry with materialdried over magnesium sulfate
  5. concentrationconcentrated
  6. filtrationThe crude product was filtered through a pad of flash grade (32-63) silica gel
  7. washeluted with 1:9 ether

出典と根拠

ORDレコード
ord-b5ae44ad9b114018befd6bf62c2be929
出典データセット
uspto-grants-1996_10
特許番号
US05563163

関連ノート

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