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Triethylamine → 6-Methoxy-1,2,3,4-tetrahydronaphthalene-2-carboxamide

HRID 654236
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HRID 654236 반응식
C([N:3](CC)CC)C.ClC(OCC)=O.[CH3:14][O:15][C:16]1[CH:17]=[C:18]2[C:23](=[CH:24][CH:25]=1)[CH2:22][CH:21]([C:26]([OH:28])=O)[CH2:20][CH2:19]2.[NH4+].[OH-]>CC(C)=O>[CH3:14][O:15][C:16]1[CH:17]=[C:18]2[C:23](=[CH:24][CH:25]=1)[CH2:22][CH:21]([C:26]([NH2:3])=[O:28])[CH2:20][CH2:19]2
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참가 물질

6

반응물 4

HCID 8471TriethylamineHCID 10928Ethyl chloroformateHCID 14923Ammonium HydroxideHCID 113562126-methoxy-1,2,3,4-tetrahydronaphthalene-2-carboxylic Acid

생성물 1

HCID 131339086-Methoxy-1,2,3,4-tetrahydronaphthalene-2-carboxamide수율 59.2%

시약·촉매·용매 1

HCID 180
Acetone
용매
2회

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온도
-10 °C

실험 절차

A solution of triethylamine (2.7 ml, 0.019 mol) and ethyl chloroformate (2 ml, 0.021 mol) in acetone (40 ml) is added to a solution of the acid obtained in step (i) (3 g, 0.014 mol) in acetone (50 ml) cooled to -10° C. After 1,5 hours at -10° C., concentrated NH4OH (4.5 ml, 0.036 mol) is added dropwise and the reaction mixture is allowed to stand at -10° C. for 1 hour and at room temperature overnight. The solution is concentrated under vacuum, ethyl acetate (150 ml) is added to the obtained residue and the solution is washed sequentially with water, a saturated sodium bicarbonate solution, 6N hydrochloric acid, and water, then it is dried and concentrated to dryness. The residue is triturated with isopropyl ether and filtered thus affording 1.7 g of the above indicated amide; m.p. 136°-138° C.; [α]=+40.2° (c= 1.4%, CHCl3).

후처리

  1. waitAfter 1,5 hours at -10° C.
  2. concentrationThe solution is concentrated under vacuum, ethyl acetate (150 ml)
  3. additionis added to the obtained residue
  4. washthe solution is washed sequentially with water
  5. dry with materiala saturated sodium bicarbonate solution, 6N hydrochloric acid, and water, then it is dried
  6. concentrationconcentrated to dryness
  7. customThe residue is triturated with isopropyl ether
  8. filtrationfiltered thus

출처 및 근거

ORD 기록
ord-fc13c33b733949479443c67588df05c4
출처 데이터셋
uspto-grants-1992_07
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US05130339

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