4-Methylmorpholine → Methyl 2-amino-4-(hydroxymethyl)benzoate

HRID 1441612ノート

反応式

HRID 1441612 の反応式
[NH2:1][C:2]1[CH:11]=[C:10]([C:12]([O-])=[O:13])[CH:9]=[CH:8][C:3]=1[C:4]([O:6][CH3:7])=[O:5].CN1CCOCC1.[BH4-].[Na+].[OH-].[Na+]>COCCOC.O>[CH3:7][O:6][C:4](=[O:5])[C:3]1[CH:8]=[CH:9][C:10]([CH2:12][OH:13])=[CH:11][C:2]=1[NH2:1]

参加物

7

反応物 4

HCID 79724-MethylmorpholineHCID 14798Sodium HydroxideHCID 4311764Sodium borohydrideHCID 21924002HCID 21924002、化合物

生成物 1

HCID 602338Methyl 2-amino-4-(hydroxymethyl)benzoate収率 86.2%

試薬・触媒・溶媒 2

HCID 962Water溶媒2 回HCID 80711,2-Dimethoxyethane溶媒

反応条件

温度
-15 °C

実験手順

To a solution of 1-methyl 2-aminoterephthalate (10.0 g, 51.2 mmol) and NMM (5.75 mL, 1 equiv) in DME (90 mL) at −15° C. was added dropwise IBCl (6.7 mL, 1 equiv). The mixture was stirred at this temperature for 15 min. The salt was removed by filtration and the solution was cooled down to −15° C. A solution of NaBH4 (3.06 g, 1.5 equiv) in water (30 mL) was added carefully dropwise. At the end of the addition, water (100 mL) was added and the mixture was stirred at r.t. for 15 min. Aq NaOH (2N, 50 mL) was added and the aqueous phase was extracted twice with AcOEt. The organic phase were combined and dried (Na2SO4). The solution was concentrated in vacuo to afford a white solid (8.0 g, 86%) (ES-MS: m/z 182.1 [M+H]+, rt 3.50 min).

後処理

  1. customThe salt was removed by filtration
  2. additionwas added
  3. stirringthe mixture was stirred at r.t. for 15 min
  4. extractionthe aqueous phase was extracted twice with AcOEt
  5. dry with materialdried (Na2SO4)
  6. concentrationThe solution was concentrated in vacuo

出典と根拠

ORDレコード
ord-cb56a9e4621b4309afd2448643e00c06
出典データセット
uspto-grants-2010_02
特許番号
US07655666B2

反応ノート

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