Acetic Acid → Entacapone Impurity 9

HRID 132018

반응식

HRID 132018 반응식
[CH2:1]([O:3][C:4]1[CH:5]=[C:6]([CH:9]=[C:10]([N+:13]([O-:15])=[O:14])[C:11]=1[OH:12])[CH:7]=O)C.C(N[N:19](NCC)[C:20](=[O:24])[CH2:21][C:22]#[N:23])C.[C:28](O)(=O)[CH3:29].N1CCC[CH2:34][CH2:33]1>C1(C)C=CC=CC=1>[CH2:33]([N:19]([CH2:28][CH3:29])[C:20](=[O:24])[C:21]([C:22]#[N:23])=[CH:7][C:6]1[CH:9]=[C:10]([N+:13]([O-:15])=[O:14])[C:11]([OH:12])=[C:4]([O:3][CH3:1])[CH:5]=1)[CH3:34]

참가 물질

6

반응물 4

HCID 176Acetic AcidHCID 8082PiperidineHCID 5848783-Ethoxy-4-hydroxy-5-nitrobenzaldehyde2회HCID 866114042-cyano-N,N-bis(ethylamino)acetamide

생성물 1

HCID 67020297Entacapone Impurity 9수율 162%

시약·촉매·용매 1

HCID 1140Toluene용매

반응 조건

온도
107.5 °C

실험 절차

A flask was charged with 3-methoxy-4-hydroxy-5-nitrobenzaldehyde (25 g, 0.126 mole) (formula 2 where R is methyl) and N,N-diethylaminocyanoacetamide (formula (3)) (22.2 g, 0.158 mole), acetic acid (4.18 g) and piperidine (5.94 g), along with toluene (250 mL) and was heated to a reflux temperature of about 105-110° C. Water was removed azeotrophically for 15 hours. The reaction mixture was concentrated and quenched into dilute hydrochloric acid and chilled water (375 mL), and stirred for 3 hours. The precipitated solid was filtered and dried to provide 36 g (88.95% yield, HPLC purity of 94.2% (including isomer)) of the N,N-diethyl-2-cyano-3-(3-methoxy-4-hydroxy-5-nitrophenyl)acrylamide, which was used as such for the next stage.

후처리

  1. customWater was removed azeotrophically for 15 hours
  2. concentrationThe reaction mixture was concentrated
  3. customquenched into dilute hydrochloric acid
  4. temperaturechilled water (375 mL)
  5. filtrationThe precipitated solid was filtered
  6. customdried

출처 및 근거

ORD 기록
ord-c0c4ef51be6f4c81bd6f0dd9cfc72a5f
출처 데이터셋
uspto-grants-2008_06
특허 번호
US07385072B2

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