Potassium Iodide → 3-Methoxy-4-(3-morpholinopropoxy)benzoic acid

HRID 1597209노트

반응식

HRID 1597209 반응식
[OH:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[CH:4][C:3]=1[O:11][CH3:12].[O:13]1[CH2:18][CH2:17][N:16]([CH2:19][CH2:20][CH2:21]Cl)[CH2:15][CH2:14]1.C(=O)([O-])[O-].[K+].[K+].[I-].[K+]>CN(C=O)C>[CH3:12][O:11][C:3]1[CH:4]=[C:5]([CH:9]=[CH:10][C:2]=1[O:1][CH2:21][CH2:20][CH2:19][N:16]1[CH2:17][CH2:18][O:13][CH2:14][CH2:15]1)[C:6]([OH:8])=[O:7]

참가 물질

6

반응물 4

HCID 4875Potassium IodideHCID 8468Vanillic AcidHCID 11430Potassium CarbonateHCID 958344-(3-Chloropropyl)morpholine

생성물 1

HCID 216992843-Methoxy-4-(3-morpholinopropoxy)benzoic acid수율 109.3%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

반응 조건

온도
100 °C

실험 절차

A mixture of 4-hydroxy-3-methoxybenzoic acid (4.5 g, 26.8 mmol), 3-morpholinopropyl chloride (9.5 g, 58.0 mmol), (prepared according to J. Am. Chem. Soc. 1945, 67, 736), potassium carbonate (8.0 g, 58 mmol), potassium iodide (1.0 g, 0.22 mmol) and DMF (80 ml) was stirred and heated at 100° C. for 3 hours. The solid was removed by filtration and the volatiles were removed from the filtrate by evaporation. The residue was dissolved in ethanol (50 ml), 2M sodium hydroxide (50 ml) was added and the mixture was heated at 90° C. for 2 hours. After partial evaporation, the mixture was acidified with concentrated hydrochloric acid, washed with ether and then subjected to purification on a Diaion (trade mark of Mitsubishi) HP20SS resin column, eluting with water and then with a gradient of methanol (0 to 25%) in hydrochloric acid (pH2). Partial evaporation of the solvents and lyophilisation gave 3-methoxy-4-(3-morpholinopropoxy)benzoic acid (8.65 g, 97%).

후처리

  1. customThe solid was removed by filtration
  2. customthe volatiles were removed from the filtrate by evaporation
  3. dissolutionThe residue was dissolved in ethanol (50 ml)
  4. addition2M sodium hydroxide (50 ml) was added
  5. temperaturethe mixture was heated at 90° C. for 2 hours
  6. customAfter partial evaporation
  7. washwashed with ether
  8. customsubjected to purification on a Diaion (trade mark of Mitsubishi) HP20SS resin column
  9. washeluting with water
  10. customPartial evaporation of the solvents and lyophilisation

출처 및 근거

ORD 기록
ord-032e2f981db2462197ebc1997c469494
출처 데이터셋
uspto-grants-2001_09
특허 번호
US06294532B1

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