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

HRID 1441612노트

반응식

HRID 1441612 반응식
[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]

참가 물질

7

반응물 4

HCID 79724-MethylmorpholineHCID 14798Sodium HydroxideHCID 4311764Sodium borohydrideHCID 21924002HCID 21924002, 화합물

생성물 1

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

시약·촉매·용매 2

HCID 962Water용매2회HCID 80711,2-Dimethoxyethane용매

반응 조건

온도
-15 °C

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-cb56a9e4621b4309afd2448643e00c06
출처 데이터셋
uspto-grants-2010_02
특허 번호
US07655666B2

반응 노트

불러오는 중…