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

HRID 654236
ノート
印刷プレビュー

反応式

HRID 654236 の反応式
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
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

6

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 180
Acetone
溶媒
2 回

反応条件

温度
-10 °C

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-fc13c33b733949479443c67588df05c4
出典データセット
uspto-grants-1992_07
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US05130339

反応ノート

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