N,N-Diethylaniline → 2-Hydroxy-1-naphthamide

HRID 393572

反応式

HRID 393572 の反応式
CC[N:3](C1C=CC=CC=1)CC.[OH:12][C:13]1[CH:22]=[CH:21][C:20]2[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=2)[C:14]=1[C:23]([OH:25])=O.Cl.CN(C)CCCN=C=NCC.ON1C2C=CC=CC=2N=N1>C1COCC1>[OH:12][C:13]1[CH:22]=[CH:21][C:20]2[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=2)[C:14]=1[C:23]([NH2:3])=[O:25]

参加物

6

反応物 4

HCID 7061N,N-DiethylanilineHCID 167902-Hydroxy-1-naphthoic acidHCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride

生成物 1

HCID 151052242-Hydroxy-1-naphthamide収率 345.7%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

反応条件

温度
23 °C

実験手順

Diethylaniline (0.27 μL, 1.7 μmol, 1.1 equiv) was added in one portion to a stirred solution of the amine (0.8 mg, 1.5 μmol, 1 equiv) in THF (0.2 mL) at 0° C. under an argon atmosphere and the solution was stirred for 5 min. 2-Hydroxy-1-naphthoic acid (0.37 mg, 2.0 μmol, 1.3 equiv), 1-[3-(dimethylamino)propyl]-3-ethylcarbodiimide hydrochloride (0.38 mg, 2.0 μmol, 1.3 equiv) and 1-hydroxybenzotriazole (0.25 mg, 1.8 μmol, 1.2 equiv) were then added separately, each in one portion, to the above solution at 0° C. The reaction mixture was warmed to 23° C. over 13 h 20 min, then was quenched with saturated aqueous ammonium chloride solution (3 mL). The mixture was diluted with ethyl acetate (10 mL) and the layers were separated. The aqueous layer was extracted with ethyl acetate (10 mL) and the combined organic layer was dried over sodium sulfate. Concentration in vacuo left a white solid, which was purified by flash column chromatography (85% ethyl acetate-hexanes) to give the 2-hydroxy-naphthalene-1-carboxylic acid amide derivative (1.1 mg, 100%) as a white solid.

後処理

  1. customat 0° C
  2. customwas quenched with saturated aqueous ammonium chloride solution (3 mL)
  3. additionThe mixture was diluted with ethyl acetate (10 mL)
  4. customthe layers were separated
  5. extractionThe aqueous layer was extracted with ethyl acetate (10 mL)
  6. dry with materialthe combined organic layer was dried over sodium sulfate
  7. concentrationConcentration in vacuo
  8. waitleft a white solid, which
  9. customwas purified by flash column chromatography (85% ethyl acetate-hexanes)

出典と根拠

ORDレコード
ord-3b78a769ebff43a498e45b363e11f4fc
出典データセット
uspto-grants-2004_10
特許番号
US06809099B2

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