1,2,3,4-Tetrahydroisoquinoline → Benzamide, N-(1,2,3,4-tetrahydro-2-methylisoquinolin-7-yl)-3,4,5-trimethoxy-

HRID 2397936노트

반응식

HRID 2397936 반응식
[NH2:1][C:2]1[CH:11]=[C:10]2[C:5]([CH2:6][CH2:7][N:8]([CH3:12])[CH2:9]2)=[CH:4][CH:3]=1.C1(C)C=CC(S([O-])(=O)=O)=CC=1.[N+](C1C=C2C(C=C[N+](C)=C2)=CC=1)([O-])=O.C(=O)(O)[O-].[K+].[CH3:43][O:44][C:45]1[CH:46]=[C:47]([CH:51]=[C:52]([O:56][CH3:57])[C:53]=1[O:54][CH3:55])[C:48](Cl)=[O:49].C1C2C(=CC=CC=2)CCN1>C1C=CC=CC=1.C(=O)([O-])[O-].[Na+].[Na+]>[CH3:57][O:56][C:52]1[CH:51]=[C:47]([CH:46]=[C:45]([O:44][CH3:43])[C:53]=1[O:54][CH3:55])[C:48]([NH:1][C:2]1[CH:11]=[C:10]2[C:5]([CH2:6][CH2:7][N:8]([CH3:12])[CH2:9]2)=[CH:4][CH:3]=1)=[O:49]

참가 물질

8

반응물 5

HCID 70461,2,3,4-TetrahydroisoquinolineHCID 78282Benzoyl chloride, 3,4,5-trimethoxy-HCID 516893Potassium BicarbonateHCID 129995062-Methyl-1,2,3,4-tetrahydroisoquinolin-7-amineHCID 21436756HCID 21436756, 화합물

생성물 1

HCID 216591Benzamide, N-(1,2,3,4-tetrahydro-2-methylisoquinolin-7-yl)-3,4,5-trimethoxy-

시약·촉매·용매 2

HCID 241Benzene용매2회HCID 10340Sodium Carbonate용매

실험 절차

7-Amino-2-methyl-1,2,3,4-tetrahydroisoquinoline (2 g), prepared from 7-nitro-2-methyl-isoquinolinium p-toluenesulfonate as described for the 5-nitro isomer in Example 4 was dissolved in dry benzene (50 ml) and 0.5 g of dry potassium bicarbonate was added. A 0.1 mole excess of 3,4,5-trimethoxybenzoyl chloride was dissolved in benzene (50 ml) and this solution was added to the solution of the tetrahydroisoquinoline. A brown precipitate formed immediately and the mixture was refluxed for 3 hours. The benzene was removed in vacuo leaving a tan residue which was suspended in 10% sodium carbonate solution to remove excess acid chloride and stirred for 1 hour. The insoluble residue was a brown oil which was extracted from the aqueous sodium carbonate with chloroform. The chloroform was dried over anhydrous magnesium sulfate and the chloroform was distilled off to leave a viscous red oil which crystallized to a white powder (2.7 g) when washed with cold ether. The white solid was recrystallized from ethanol-ether to yield the desired product as a white powder, m.p. 157.5°-158° C.

후처리

  1. customA brown precipitate formed immediately
  2. temperaturethe mixture was refluxed for 3 hours
  3. customThe benzene was removed in vacuo
  4. customleaving a tan residue which
  5. customto remove excess acid chloride
  6. extractionwas extracted from the aqueous sodium carbonate with chloroform
  7. dry with materialThe chloroform was dried over anhydrous magnesium sulfate
  8. distillationthe chloroform was distilled off
  9. customto leave a viscous red oil which
  10. customcrystallized to a white powder (2.7 g) when
  11. washwashed with cold ether
  12. customThe white solid was recrystallized from ethanol-ether

출처 및 근거

ORD 기록
ord-7a8c5ea54e784e42bda22c23f477b0d8
출처 데이터셋
uspto-grants-1977_05
특허 번호
US04022900

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