7-Methoxy-1,2,3,4-tetrahydronaphthalen-1-one → 7-Methoxynaphthalene-1-carbonitrile

HRID 226269노트

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HRID 226269 반응식
FC1C=C([C:9]2[CH:10]=[C:11]([C:20]#[N:21])[C:12]3[C:17]([CH:18]=2)=[CH:16][CH:15]=[C:14]([OH:19])[CH:13]=3)C=CC=1O.[CH3:22]OC1C=C2C(CCCC2=O)=CC=1>C1(C)C=CC=CC=1>[CH3:22][O:19][C:14]1[CH:13]=[C:12]2[C:17]([CH:18]=[CH:9][CH:10]=[C:11]2[C:20]#[N:21])=[CH:16][CH:15]=1

참가 물질

4

반응물 2

HCID 812767-Methoxy-1,2,3,4-tetrahydronaphthalen-1-oneHCID 61026913-(3-Fluoro-4-hydroxyphenyl)-7-hydroxy-1-naphthonitrile

생성물 1

HCID 113443927-Methoxynaphthalene-1-carbonitrile

시약·촉매·용매 1

HCID 1140Toluene용매

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온도
60 °C

실험 절차

In a highly preferred aspect of this invention illustrated in Scheme 1, there is provided a new and improved process for the large-scale production of 3-(3-fluoro-4-hydroxyphenyl)-7-hydroxy-1-naphthonitrile (1). Commercial material 3,4-dihydro-7-methoxy-1(2H)-naphthalenone (7-methoxy-1-tetralone) may be transformed into an unsaturated nitrile (3) as shown on Scheme 1. The reaction is performed in toluene solution. Upon the completion of the reaction, it is quenched by caustic solution. The reaction mixture is extracted with toluene. After washing the toluene solution, the crude unsaturated nitrile (3) is aromatized directly in this toluene solution by stirring with 2,3-dichloro-5,6-dicyano-1,4-benzoquinone (DDQ) at 60° C. for 2 h. The solid is removed by filtration and the filtrate is washed with sodium hydroxide solution and brine and respectively. Most of the solvent is removed by distillation and heptane is added to precipitate the product. 7-methoxy-1-naphthonitrile (4) is isolated. The expected yield over these two steps is at least 70-75%. By performing two reactions in the same solvent, isolation of the low melting point intermediate (3) can be avoided, improving efficiency and yield.

후처리

  1. customUpon the completion of the reaction, it
  2. customis quenched by caustic solution
  3. extractionThe reaction mixture is extracted with toluene
  4. washAfter washing the toluene solution
  5. customThe solid is removed by filtration
  6. washthe filtrate is washed with sodium hydroxide solution and brine
  7. customMost of the solvent is removed by distillation and heptane
  8. additionis added
  9. customto precipitate the product

출처 및 근거

ORD 기록
ord-695cb9dbe6894511be953e5c9b09923a
출처 데이터셋
uspto-grants-2009_07
특허 번호
US07557237B2

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