Borane → Methyl 3-(aminomethyl)-5-nitrobenzoate

HRID 964486

반응식

HRID 964486 반응식
[CH3:1][O:2][C:3]([C:5]1[CH:6]=[C:7]([CH:11]=[C:12]([N+:14]([O-:16])=[O:15])[CH:13]=1)[C:8]([NH2:10])=O)=[O:4].B>C1COCC1>[N+:14]([C:12]1[CH:13]=[C:5]([CH:6]=[C:7]([CH2:8][NH2:10])[CH:11]=1)[C:3]([O:2][CH3:1])=[O:4])([O-:16])=[O:15]

참가 물질

4

반응물 2

HCID 6331BoraneHCID 3741295Methyl 3-carbamoyl-5-nitrobenzoate

생성물 1

HCID 19077132Methyl 3-(aminomethyl)-5-nitrobenzoate수율 34.4%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

A mixture of 3-methoxycabonyl-5-nitrobenzamide (1120 mg, 5 mmol) and 1M BH3 in THF (11.5 mL) was refluxed for 90 minutes. For a detailed description of techniques for borane reduction, see Brown, H. C.; Heim, P. J. Org. Chem. 1973, 38, 912-916. The solvent was evaporated and MeOH (15 mL) was added. HCl gas was introduced into the solution and the reaction mixture was refluxed for 70 minutes. The mixture was added saturated NaHCO3 aq. (50 mL) and extracted with CH2Cl2 (5×40 mL). The organic layers were combined, washed with brine and dried over Na2SO4. The dried solution was applied directly to SiO2 column and developed with AcOEt then 1/10=MeOH/AcOEt. The elution was evaporated to give the desired product (361 mg, 34%): 1H NMR (300 MHz, CDCl3) δ 8.696 (s, 1H), 8.403 (s, 1H), 8.320 (s, 1H), 4.051 (s, 2H), 3.961 (s, 3H); 13C NMR (300 MHz, CDCl3) δ 165.0, 148.3, 145.9, 133.7, 131.7, 125.8, 122.8, 52.7, 45.2; HRMS m/e calc'd for C9H10 N2O4 : 209.0562, found 209.0565.

후처리

  1. customThe solvent was evaporated
  2. additionMeOH (15 mL) was added
  3. additionHCl gas was introduced into the solution
  4. temperaturethe reaction mixture was refluxed for 70 minutes
  5. additionThe mixture was added saturated NaHCO3 aq. (50 mL)
  6. extractionextracted with CH2Cl2 (5×40 mL)
  7. washwashed with brine
  8. dry with materialdried over Na2SO4
  9. washThe elution
  10. customwas evaporated

출처 및 근거

ORD 기록
ord-93bfef2903de4debb331a69d53004077
출처 데이터셋
uspto-grants-1998_06
특허 번호
US05770380

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