Tetralin → 3-(N-Propionyl)amino-1,2,3,4-tetrahydroquinoline

HRID 266169

반응식

HRID 266169 반응식
[C:1]([NH:5][C:6]1[CH:7]=[N:8][C:9]2[C:14]([CH:15]=1)=[CH:13][CH:12]=[CH:11][CH:10]=2)(=[O:4])[CH2:2][CH3:3].C([O-])=O.[NH4+].C1C2C(=CC=CC=2)CCC1.ClC1C=CC=C2C=1CC(NCCC)CC2>CO.[Pd]>[C:1]([NH:5][CH:6]1[CH2:15][C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[NH:8][CH2:7]1)(=[O:4])[CH2:2][CH3:3]

참가 물질

7

반응물 4

HCID 8404TetralinHCID 2723923Ammonium formateHCID 149692298-chloro-2-(N-n-propylamino)tetralin2회HCID 19032664N-(Quinolin-3-Yl)propanamide

생성물 1

HCID 196976643-(N-Propionyl)amino-1,2,3,4-tetrahydroquinoline

시약·촉매·용매 2

HCID 23938Palladium촉매HCID 887Methanol용매

실험 절차

To a solution of 17.4 g (86.9) 3-(N-propionyl)aminoquinoline and 20.0 g (317 mmol) ammonium formate in 150 ml methanol was added 1.0 g Pd/C cautiously under an inert atmosphere. After stirring at ambient temperature for 2 days the reaction stopped. The ratio between starting material and product was approximately 1:1 (monitored by GLC). The mixture was filtered on Celite and evaporated to a residue from which the product was extracted into diethyl ether. The ether solution was dried (magnesium sulfate), filtered and evaporated. The product/starting material mixture was then recharged in a similar manner using the same amounts of reactants. After additional 4 days the reaction was completed and worked-up as above to yield 9.7 g (55%) of reasonably pure material: MS m/e 204 (M+, 4), 130 (100), 131 (45), 118 (8), 91 (5), 77 (5).

후처리

  1. filtrationThe mixture was filtered on Celite
  2. customevaporated to a residue from which the product
  3. extractionwas extracted into diethyl ether
  4. dry with materialThe ether solution was dried (magnesium sulfate)
  5. filtrationfiltered
  6. customevaporated
  7. waitAfter additional 4 days the reaction was completed
  8. customto yield 9.7 g (55%) of reasonably pure material

출처 및 근거

ORD 기록
ord-731482a71cee432ba4e77138994a5a50
출처 데이터셋
uspto-grants-1997_07
특허 번호
US05650427

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