Formic Acid → Benzoic acid, 3-(methylamino)-, methyl ester

HRID 1055331노트

반응식

HRID 1055331 반응식
[CH:1](O)=O.C(OC(=O)C)(=O)C.[NH2:11][C:12]1[CH:13]=[C:14]([CH:19]=[CH:20][CH:21]=1)[C:15]([O:17][CH3:18])=[O:16].CSC.B>C1COCC1.CO>[CH3:1][NH:11][C:12]1[CH:13]=[C:14]([CH:19]=[CH:20][CH:21]=1)[C:15]([O:17][CH3:18])=[O:16]

참가 물질

7

반응물 4

HCID 284Formic AcidHCID 7918Acetic AnhydrideHCID 78274Benzoic acid, 3-amino-, methyl esterHCID 12423031(Dimethyl sulfide)trihydroboron

생성물 1

HCID 10899041Benzoic acid, 3-(methylamino)-, methyl ester

시약·촉매·용매 2

HCID 887Methanol용매HCID 8028Tetrahydrofuran용매

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온도
0 °C

실험 절차

A solution of formic acid (106 mL) and acetic anhydride (53.0 mL) was stirred at room temperature for 1 h. Methyl 3-aminobenzoate (8.50 g, 56.2 mmol) was added and the resulting mixture was stirred overnight. The reaction mixture was then concentrated under reduced pressure to give a solid. The solid was dissolved in THF (50.0 mL) and this solution was cooled to 0° C. Borane dimethylsulfide (10.7 mL, 112 mmol) was added slowly and the resulting mixture was stirred at room temperature overnight. The reaction mixture was then cooled to 0° C. and MeOH (10 mL) was added slowly. This mixture was stirred for 3 hours and then concentrated under reduced pressure to give the title compound, which was used without any further purification.

후처리

  1. concentrationThe reaction mixture was then concentrated under reduced pressure
  2. customto give a solid
  3. stirringthe resulting mixture was stirred at room temperature overnight
  4. temperatureThe reaction mixture was then cooled to 0° C.
  5. stirringThis mixture was stirred for 3 hours
  6. concentrationconcentrated under reduced pressure

출처 및 근거

ORD 기록
ord-236e81a43ed442df90b38e2777da0966
출처 데이터셋
uspto-grants-2016_07
특허 번호
US09394275B2

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